Palladium Catalyzed Regioselective C4-Arylation and Olefination of Indoles and Azaindoles

Neetipalli Thrimurtulu,a Arnab Dey,a Anurag Singh,a Kuntal Pal,a
Debabrata Maiti,a,* and Chandra M. R. Vollaa,* a Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076, India
Phone: +91-2225767188
Fax: +91-2225767152
E-mail: [email protected]; [email protected]
Manuscript received: October 11, 2018; Revised manuscript received: December 24, 2018;
Version of record online: February 5, 2019

In the past decade, directing group assisted CH activation has been established as an extremely powerful and efficient strategy for accessing complex heterocyclic skeletons.[1] Successful execution of these approaches is also finding applications in natural product synthesis.[2] Recently, more challenging distal CH bond functionalization gained a lot of attention.[3] Although excellent progress was made in the transition-metal catalyzed CH activation reactions facilitating a variety of directing groups, only limited reports were available for the aldehyde-directed CH functionalization, probably due to the weak coordinating ability of the carbonyl group.[4] This issue is often addressed by converting the aldehyde group into more competent imine or oxime-directing groups.[5] However, such methods require additional synthetic steps for the installation and removal of the directing group, which impede the overall reaction efficiency. An alternative strategy of forming the directing group transiently, which will reversibly bind to the metalcatalyst was suggested by Jun and co-workers for the Rh-catalyzed hydroacylation of alkenes with aldehydes.[6,7] Following similar approach, Yu and coworkers described an elegant a-amino acid mediated Pd(II)-catalyzed sp3 CH arylation of o-tolualdehydes and aliphatic ketones.[8] The bidentate chelation of imine nitrogen and carboxylate moiety to Pd(II)-catalyst enables the activation of CH bonds. Later, the groups of Hu[9] and Ge[10] also demonstrated sp3 CH arylation reactions of aliphatic aldehydes using acetohydrazone and 3-aminopropanoic acid as transient directing groups respectively. Pd(II)-catalyzed sp2 CH activation of benzaldehyde derivatives was realized by Sorensen and co-workers for the synthesis of fluorenones.[11] Very recently, direct ortho sp2 CH arylation of aryl ketones was illustrated by Jin and coworkers using glycine.[12] Despite these advances, transient directing group mediated Pd(II)-catalyzed CH functionalization reactions were largely limited to aryl rings.[13] Implementation of this strategy for the CH activation of heteroaryl rings was less studied.

On the other hand, indole and azaindole skeletons are widely present in many natural and unnatural biologically active compounds and pharmaceuticals (Figure 1).[14] Transition-metal catalyzed regioselective CH functionalization of indoles would offer a direct approach for the construction of diverse array of indole skeletons.[15] Functionalization of indoles at the C3 and C2-positions were well established due to the high electron density of the pyrrolic ring. In contrast, diversification of the benzenoid moiety of indoles and related heterocycles such as azaindoles at C4, C5, C6 and C7 positions has been gaining prominence only recently.[16] Inspired by the broad occurrence of C4-substituted indole skeletons, we envisioned developing a transient directing group mediated bidentate chelation strategy for the sp2 CH functionalization at the C4-position of indole-3-carbaldehydes. The initial challenge associated with the envisioned project was the potential competition of C4 position with C2
position. 

The importance of C4-decorated indoles in natural product synthesis, materials science and medicinal chemistry inspired several groups to study regioselective direct C4 functionalization of indoles. In 2013,
Prabhu and co-workers reported a C4-H alkenylation of 3-formylindoles using Ru(II)-salts (Scheme 1a).[17] Jia and co-workers developed Rh(III)-catalyzed olefination of unprotected indoles and demonstrated its application in the synthesis of ()-agroclavine and ()-elymoclavine.[18] Around the same time, an Ir(III)-catalyzed C4-amidation was illustrated by You and coworkers using sulfonyl azides (Scheme 1b).[19] Shi and co-workers established an elegant Pd(0)-catalyzed strategy for the C4-arylation of indoles using pivaloyl directing group (Scheme 1c).[20] A single example of a transient directing group mediated C4-arylation of Ntosyl-3-fomylindole was reported by Yu and co-workers (Scheme 1d).[21] In spite of these elegant reports, development of a general Pd-catalyzed C4-selective arylation and olefination of indoles and azaindoles is highly desirable (Scheme 1e).

We began the investigation using cheap and commercially available glycine as the transient directing group for the C4-arylation of N-benzyl-1H-indole-3-carbaldehyde 1 a with iodobenzene 5 a. [22] Using
10 mol% of Pd(OAc)2 and 2.0 equiv. of AgTFA at 110 8C, initial solvent screening was carried out and we were delighted to see the formation of desired product 6 a as a single regioisomer in 69% of NMR
yield in a 1:1 solvent mixture of AcOH and HFIP (hexafluoroisopropanol). Compound 6 a was unambiguously characterized through X-ray crystallography.[23]

The arylation proceeded exclusively at the C4-position by selective formation of a six-membered palladacycle intermediate (vide infra). No C2-arylation product was observed in the 1 H NMR of the crude reaction mixture. Based on the observation by Yu and coworkers,[8] we tested the effect of H2O additive in the transient directing group mediated C4-arylation and indeed using an esoteric mixture of AcOH/HFIP/H2O (1:1:0.1, v/v), we observed the formation of 6 a in an improved NMR yield of 86% (isolated yield of 82%).

The effect of glycine as a transient directing group is evident as in the absence of glycine no reaction was observed. Other amino carboxylic or sulfonic acids were also tested instead of glycine, however only
lower yields were observed in these cases. Using glycine methyl ester instead of glycine led to no reaction indicating the importance of the carboxylic acid moiety for the formation of 5-membered palladacycle intermediate.

To evaluate the generality of this new transformation, we tested the role of nitrogen protecting groups (Scheme 2). Unprotected or N-methyl or N-tosyl protected 3-formylindoles 2–4 provided the corresponding C4-arylated products 7 a–9 a in 48%, 79% and 80% respectively (Scheme 2).

In order to thoroughly outline the utility of this method, we systematically tested a number of aryl iodides. A wide variety of electron rich and electron poor aryl iodides were investigated. As shown in Scheme 3, the reaction is compatible with a range of substituents and 4-tert-butylphenyl iodide (6 d) and 4-biphenyl iodide (6 e) did not affect the yield and selectivity. Several valuable functional groups such as acetyl (6 f), hydroxyl (6 g), methoxy (6 h, 6i), trifluoromethyl (6 j), keto (6 k, 7 k) and nitro (6l) groups were well tolerated at different positions of the aromatic ring. Hydroxy substituent in the ortho-position of aryliodide resulted in only a moderate yield of 68% (6 g) probably because of both unfavourable electronic and steric effects.

We further elaborated the scope of this reaction with differently substituted 3-formylindoles (Scheme 4). Notably, 2-methyl substituted indole derivative led to selective sp2 CH activation to afford the corresponding products 6m, 6 n in 82% and 80% respectively. This clearly indicates the preferential formation of cyclic six membered palladacycle intermediate by C4H sp2 CH activation. The reaction
was also applicable to 6-aryl substituted indolyl aldehydes (6 o–6 r). Intriguingly, 6-chloro and 6-bromo indoles provided the corresponding functionalized products (6 s–6 v) in synthetically useful yields. The
structures of 6 s and 6 v were confirmed unambiguously by X-ray crystallography.[23] In the case of C5-substituted indole, the reaction was sluggish and even after prolonged heating, no product was observed probably because of increased steric hindrance.

The versatility of this Pd(II)-catalyzed CH activation was further expanded to biologically active and therapeutically important azaindole core (Scheme 5).[24] As expected, N-methyl azaindole derivative 10 a underwent the CH activation to provide C-4 arylated azaindole 11 a in 61% using 10 mol% of Pd(OAc)2. The scope of the reaction with N-benzyl protected azaindole aldehyde 10 b was investigated with iodobenzene (11 b, 45%) and 4-phenyl-iodobenzene (11 c, 51%).

Gratifyingly, the reaction was not limited to aryl iodides and alkenyl iodides also under the optimized reaction conditions found to be useful partners furnishing the corresponding 4-alkenylated indoles 13.
As demonstrated in Scheme 6, use of 10 mol% of Pd(OAc)2 and glycine as the transient directing group allowed the CH olefination at C-4 position of Nbenzyl or N-methyl-indole-3-carbaldehydes with
benzyl-trans-3-iodoacrylate 12 to afford 13 a–d in 55–63%.

To study the scalability of the present method, the reaction of 1 v (1.0 g) with 5 a was performed on a gram scale and 6 v was obtained in 63% yield (0.78 g). The synthetic utility of the C4-arylated indole derivatives was demonstrated by carrying out SuzukiMiyaura coupling of 6 v with phenylboronic acid 14gram scale and 6 v was obtained in 63% yield (0.78 g). The synthetic utility of the C4-arylated indole derivatives was demonstrated by carrying out SuzukiMiyaura coupling of 6 v with phenylboronic acid 14 and 6 o was isolated in 83% yield. Reduction of 6 v using 2.0 equiv. of NaBH4 gave the corresponding alcohol derivative 15 in 81% yield (Scheme 7a). The formyl directing group can be removed easily from the C4-arylated 3-formylindole 6 a under Pd(II)-catalysis to give 16 in 75% yield (Scheme 7b).[25] Our initial attempts to isolate any reaction intermediate met with no success. To gain some insights into the reaction mechanism, H/D scrambling experiments were carried out. Under the optimized reaction conditions, 1 a was treated with a mixture of CH3COOD/HFIP/D2O (1:1:0.1 v/v) and after 6 h around 7% of H/D scrambling was observed at C4-position. Interestingly,
no significant H/D exchange was observed at C2-position (Scheme 7c). Analogous experiment carried in the presence of 5 a also showed no scrambling at the C2-position of 6 a and 12% H/D exchange was
observed in the recovered starting material 1 a (Scheme 7d).

The probable reaction mechanism for the reaction is outlined in Scheme 8. Condensation of the 3-formylindole 1 with glycine provides the intermediate A. Coordination of imine nitrogen and carboxylate
moiety to Pd(II)-species leads to five membered palladacycle intermediate B. Preferential formation of [5,6]-bicyclic palladium intermediate C proceeds via a regioselective C4H activation of indoles (instead of C2H activation of indoles). Oxidative addition of aryl iodide onto intermediate C generates Pd(IV)- species D.[26] Finally reductive elimination of D and iodide abstraction by silver trifluoroacetate provides the intermediate F and regenerates the Pd(II)-catalyst. Hydrolysis of F leads to the formation of C4- substituted indolyl aldehydes and transient directing group glycine.

In summary, we have developed a transient directing group mediated Pd(II)-catalyzed CH arylation and olefination reactions of indoles, proceeding selectively at the C4-position using commercially available and cheap glycine as the transient directing group. The reaction proceeds in the presence of water under operationally simple conditions for 3-formylindoles and 3-formylazaindoles.

Experimental Section
Typical experimental procedure for the synthesis of 6 a: In an oven dried 10 mL reaction tube, charged with magnetic stirbar, Pd(OAc)2 (4.5 mg, 10 mol%), AgTFA (88 mg, 0.4 mmol), glycine (30 mg, 0.4 mmol), and N-benzyl-1Hindole-3-carbaldehyde 1 a (47 mg, 0.2 mmol) were added. Commercially available iodobenzene (122 mg, 0.6 mmol), was added was added to the reaction mixture followed by
acetic acid (1 mL), HFIP (1 mL) and water (0.1 mL) at room temperature. The reaction tube was capped and stirred at 1108C temperature for 36 hours. Upon completion, the reaction mixture was cooled to room temperature. The reaction mixture was poured into the NaHCO3 solution and extracted with ethyl acetate. The separated organic layer was dried under Na2SO4, evaporated under reduced pressure and passed through the column chromatography for purification on silica gel with petroleum ether and ethyl acetate (19:1) mixture as the eluent, giving the product 6 a (50 mg, 82% yield)

Acknowledgements
The activity is supported by DST, India (Funding to DM, SR/NM/NS-1065/2015 (G), SERB (funding to CMRV, EMR/2015/002047). Financial support was also received from DSTFast Track Young Scientist (NT), CSIR for A. S. and K. P.

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Pseudoerythromycin A enol ether Catalog No.:AA007WI3 CAS No.:105882-69-7 MDL No.: MF:C37H65NO12 MW:715.9115	5'-Bromo-2'-chloroacetophenone Catalog No.:AA008STN CAS No.:105884-19-3 MDL No.:MFCD02683851 MF:C8H6BrClO MW:233.4896
2,2-dimethylpropanoyloxymethyl 7-[[(Z)-2-(2-amino-1,3-thiazol-4-yl)pent-2-enoyl]amino]-3-(carbamoyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Catalog No.:AA01DQ7R CAS No.:105889-45-0 MDL No.:MFCD14701917 MF:C23H29N5O8S2 MW:567.6351	Pyroporphyrin dimethyl ester Catalog No.:AA002Q10 CAS No.:10589-94-3 MDL No.:MFCD00010033 MF:C32H34N4O4 MW:538.6368
3-hydroxy-2-(3-hydroxyphenyl)prop-2-enal Catalog No.:AA01DX6Q CAS No.:105899-68-1 MDL No.:MFCD31665380 MF:C9H8O3 MW:164.1580	Taraxasterol Catalog No.:AA008UZI CAS No.:1059-14-9 MDL No.:MFCD04039802 MF:C30H50O MW:426.7174
7-DEHYDROCHOLESTEROL ACETATE Catalog No.:AA008UGK CAS No.:1059-86-5 MDL No.:MFCD00053452 MF:C29H46O2 MW:426.6743	Cephalonium lactone Catalog No.:AA0091V5 CAS No.:10590-10-0 MDL No.:MFCD10566362 MF:C14H12N2O4S2 MW:336.3861
4-Methylquinoline-2-carbonitrile Catalog No.:AA0084V8 CAS No.:10590-69-9 MDL No.:MFCD08705686 MF:C11H8N2 MW:168.1946	3-Methyl-1h-indole-2-carboxylic acid Catalog No.:AA0084V7 CAS No.:10590-73-5 MDL No.:MFCD01652241 MF:C10H9NO2 MW:175.1840
1-Bromo-2-(cyclohexyloxy)benzene Catalog No.:AA0093YT CAS No.:105902-37-2 MDL No.:MFCD11167623 MF:C12H15BrO MW:255.1509	3-methyl-2-(2-methylphenyl)butanenitrile Catalog No.:AA01BD72 CAS No.:105902-47-4 MDL No.:MFCD16301515 MF:C12H15N MW:173.2542
2-(4-tert-Butylcyclohexyl)acetic acid Catalog No.:AA007EN4 CAS No.:105906-07-8 MDL No.:MFCD03414290 MF:C12H22O2 MW:198.3019	3-bromo-8-(trifluoromethyl)quinoline Catalog No.:AA0095RD CAS No.:1059064-11-7 MDL No.:MFCD25542362 MF:C10H5BrF3N MW:276.0526
2-{4-[(4-methoxyphenyl)methoxy]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Catalog No.:AA00HANG CAS No.:1059066-01-1 MDL No.:MFCD12027031 MF:C20H25BO4 MW:340.2211	3-Chloro-n-(4-methylbenzyl)propanamide Catalog No.:AA008VF2 CAS No.:105907-34-4 MDL No.:MFCD01213662 MF:C11H14ClNO MW:211.6880
4-Cyanogramine Catalog No.:AA00HANI CAS No.:105907-63-9 MDL No.:MFCD11112015 MF:C12H13N3 MW:199.2517	1-(3,5-Dimethylphenyl)piperazine Catalog No.:AA0084V6 CAS No.:105907-65-1 MDL No.:MFCD03095639 MF:C12H18N2 MW:190.2847
6-Amino-2-(butylamino)-9-[[6-[2-(dimethylamino)ethoxy]-3-pyridinyl]methyl]-7,9-dihydro-8H-purin-8-one Catalog No.:AA01ENKU CAS No.:1059070-10-8 MDL No.:MFCD30182245 MF:C19H28N8O2 MW:400.4780	3-Chloro-N-(2-methoxybenzyl)propanamide Catalog No.:AA007WEI CAS No.:105909-52-2 MDL No.:MFCD02973798 MF:C11H14ClNO2 MW:227.6874
3-oxo-2-phenylhexanenitrile Catalog No.:AA01DX6R CAS No.:105909-68-0 MDL No.:MFCD11208535 MF:C12H13NO MW:187.2377	5-Methoxy-1,2-dimethyl-1h-indole-3-carboxylic acid Catalog No.:AA0084V2 CAS No.:105909-93-1 MDL No.:MFCD00458840 MF:C12H13NO3 MW:219.2365
Tetrabenzylthiuram disulfide Catalog No.:AA0084RD CAS No.:10591-85-2 MDL No.:MFCD09842304 MF:C30H28N2S4 MW:544.8167	4-Methyl-5-(2-((4-morpholinophenyl)imino)-2,5-dihydropyrimidin-4-yl)thiazol-2-amine Catalog No.:AA008VTR CAS No.:1059105-22-4 MDL No.:MFCD14155805 MF:C18H20N6OS MW:368.4560
1-[2-Bromoethenyl]-4-(trifluoromethyl)benzene E/Z-mixture Catalog No.:AA00HANK CAS No.:1059140-27-0 MDL No.:MFCD15527444 MF:C9H6BrF3 MW:251.0431	1-(2,3-Dichloro-4-(ethylthio)phenyl)ethanone Catalog No.:AA00IQEH CAS No.:105917-69-9 MDL No.:MFCD05663800 MF:C10H10Cl2OS MW:249.1568
2,3-Dichloro-4-(ethylsulfonyl)benzoic acid Catalog No.:AA0096ES CAS No.:105917-76-8 MDL No.:MFCD01935963 MF:C9H8Cl2O4S MW:283.1284	2-morpholino-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide Catalog No.:AA01DU9U CAS No.:1059171-55-9 MDL No.:MFCD31916428 MF:C18H27BN2O4 MW:346.2290
5-(3,5-difluorophenyl)-5-methylimidazolidine-2,4-dione Catalog No.:AA01A0X5 CAS No.:1059185-97-5 MDL No.:MFCD22392110 MF:C10H8F2N2O2 MW:226.1795	M-Peg4-ch2-aldehyde Catalog No.:AA019E62 CAS No.:1059189-65-9 MDL No.:MFCD30458023 MF:C11H22O6 MW:250.2888
2-(3-Ethylureido)-2-oxoacetic acid Catalog No.:AA007WED CAS No.:105919-00-4 MDL No.:MFCD11870854 MF:C5H8N2O4 MW:160.1280	Cis-2-fluoro-cyclopropanecarboxylic acid Catalog No.:AA00HANM CAS No.:105919-34-4 MDL No.:MFCD04972869 MF:C8H10F2O4 MW:208.1594
Methyl 2-(1,3-dioxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl)acetate Catalog No.:AA00HANN CAS No.:1059195-96-8 MDL No.:MFCD28992186 MF:C10H10N2O4 MW:222.1974	Doxycycline, HCl Catalog No.:AA00HANO CAS No.:10592-13-9 MDL No.:MFCD17018844 MF:C22H25ClN2O8 MW:480.8955
2,3-Dihydro-1H-pyrrolo[2,3-b]pyridine Catalog No.:AA003FG3 CAS No.:10592-27-5 MDL No.:MFCD06659751 MF:C7H8N2 MW:120.1518	2-chloro-10-(4-methoxybenzoyl)-10H-phenothiazine Catalog No.:AA01EIFZ CAS No.:105925-39-1 MDL No.:MFCD01245092 MF:C20H14ClNO2S MW:367.8487
D-Alanine, 3-azido- Catalog No.:AA007WDS CAS No.:105928-88-9 MDL No.:MFCD01674172 MF:C3H6N4O2 MW:130.1053	1-Thio-beta-D-glucose sodium salt Catalog No.:AA007EMH CAS No.:10593-29-0 MDL No.:MFCD30749324 MF:C6H11NaO5S MW:218.2033
N4-Benzoyl-2'-deoxy-5'-O-DMT-5-methylcytidine 3'-CE phosphoramidite Catalog No.:AA008SLI CAS No.:105931-57-5 MDL No.:MFCD00148939 MF:C47H54N5O8P MW:847.9341	N6-Methyl-dAphosphoramidite Catalog No.:AA008SI8 CAS No.:105931-58-6 MDL No.:MFCD10686973 MF:C41H50N7O6P MW:767.8528
H-Val-pro-oh hcl Catalog No.:AA008RIP CAS No.:105931-64-4 MDL No.:MFCD00191045 MF:C10H19ClN2O3 MW:250.7225	4-Bromo-2-fluoro-1-iodobenzene Catalog No.:AA003E1G CAS No.:105931-73-5 MDL No.:MFCD00010608 MF:C6H3BrFI MW:300.8949
tert-Butyl 2-(trifluoromethyl)acrylate Catalog No.:AA0084QZ CAS No.:105935-24-8 MDL No.:MFCD04038275 MF:C8H11F3O2 MW:196.1669	3-(prop-2-en-1-yloxy)propan-1-amine Catalog No.:AA01B67Q CAS No.:105939-61-5 MDL No.:MFCD16663806 MF:C6H13NO MW:115.1735
(3-aminopropoxy)(methoxy)methane Catalog No.:AA01AUEE CAS No.:105939-69-3 MDL No.:MFCD19209989 MF:C5H13NO2 MW:119.1622	4-(propan-2-yloxy)butan-1-amine Catalog No.:AA01A69B CAS No.:105939-74-0 MDL No.:MFCD09803135 MF:C7H17NO MW:131.2160
4-Bromo-2-fluorobenzonitrile Catalog No.:AA0033UN CAS No.:105942-08-3 MDL No.:MFCD00143264 MF:C7H3BrFN MW:200.0078	4-Cyano-2-fluorobenzyl bromide Catalog No.:AA003H6K CAS No.:105942-09-4 MDL No.:MFCD07368341 MF:C8H5BrFN MW:214.0344
4-Cyano-2-fluorobenzaldehyde Catalog No.:AA0084QU CAS No.:105942-10-7 MDL No.:MFCD07368786 MF:C8H4FNO MW:149.1219	4-Bromo-4'-iodobiphenyl Catalog No.:AA003KVX CAS No.:105946-82-5 MDL No.:MFCD17676204 MF:C12H8BrI MW:359.0004
2-Propenoic acid,2-methyl-, 2-phenoxyethyl ester Catalog No.:AA0084QQ CAS No.:10595-06-9 MDL No.:MFCD00053685 MF:C12H14O3 MW:206.2378	Benzenamine,N-methyl-4-nitroso- Catalog No.:AA007WD7 CAS No.:10595-51-4 MDL No.:MFCD00019923 MF:C7H8N2O MW:136.1512
N-ethyl-N-methyl-nitrous amide Catalog No.:AA01CBOV CAS No.:10595-95-6 MDL No.:MFCD00015802 MF:C3H8N2O MW:88.1084	4-chloro-2-(methoxymethyl)pyrimidine Catalog No.:AA01BJ6G CAS No.:105950-89-8 MDL No.:MFCD11043805 MF:C6H7ClN2O MW:158.5856
4-(3-(Trifluoromethyl)-1H-pyrazol-1-yl)benzonitrile Catalog No.:AA01AUZT CAS No.:1059539-29-5 MDL No.:MFCD10001666 MF:C11H6F3N3 MW:237.1806	STEARDA Catalog No.:AA007EH7 CAS No.:105955-10-0 MDL No.:MFCD08703100 MF:C26H45NO3 MW:419.6404
OLDA Catalog No.:AA008RBC CAS No.:105955-11-1 MDL No.:MFCD05665144 MF:C26H43NO3 MW:417.6245	Clinafloxacin Catalog No.:AA007EH4 CAS No.:105956-97-6 MDL No.:MFCD00865120 MF:C17H17ClFN3O3 MW:365.7866
Clinafloxacin hydrochloride Catalog No.:AA008TRW CAS No.:105956-99-8 MDL No.:MFCD03840545 MF:C17H18Cl2FN3O3 MW:402.2475	2-(3-nitro-1H-1,2,4-triazol-1-yl)ethan-1-ol Catalog No.:AA019TXU CAS No.:105958-72-3 MDL No.:MFCD03059897 MF:C4H6N4O3 MW:158.1154
N-(1-Phenylethyl) Ibuprofen AMide (Mixture of 4 DiastereoMers) Catalog No.:AA008VVD CAS No.:105959-56-6 MDL No.:MFCD00399476 MF:C21H27NO MW:309.4452	Phosphonic acid, P,P'-(bromomethylene)bis- Catalog No.:AA00143G CAS No.:10596-21-1 MDL No.:MFCD11044946 MF:CH5BrO6P2 MW:254.8983
Tetraisopropyl Dichloromethylene Diphosphonate Catalog No.:AA0084QA CAS No.:10596-22-2 MDL No.:MFCD00015019 MF:C13H28Cl2O6P2 MW:413.2113	Clodronic acid Catalog No.:AA0039N1 CAS No.:10596-23-3 MDL No.:MFCD00867075 MF:CH4Cl2O6P2 MW:244.8924
Difluoromethylenediphosphonic Acid Catalog No.:AA0084Q7 CAS No.:10596-32-4 MDL No.:MFCD00233600 MF:CH4F2O6P2 MW:211.9832	3-Chloro-4-hydroxybenzyl alchol Catalog No.:AA0095JI CAS No.:105960-29-0 MDL No.:MFCD06202632 MF:C7H7ClO2 MW:158.5823
1-Allyl-1-methylpyrrolidinium bis(trifluoromethanesulfonyl)imide Catalog No.:AA00IM9S CAS No.:1059624-23-5 MDL No.:MFCD30749130 MF: MW:	[4-(Difluoromethoxy)benzyl]hydrazine dihydrochloride Catalog No.:AA0090FD CAS No.:1059626-03-7 MDL No.:MFCD06800563 MF:C8H11ClF2N2O MW:224.6355
(4-Fluorobenzyl)hydrazine hydrochloride Catalog No.:AA008YYV CAS No.:1059626-05-9 MDL No.:MFCD08458859 MF:C7H10ClFN2 MW:176.6191	(2-Methylbenzyl)hydrazine hydrochloride Catalog No.:AA00J1ED CAS No.:1059626-06-0 MDL No.:MFCD06800972 MF:C8H13ClN2 MW:172.6552
4-(hydrazinylmethyl)benzonitrile hydrochloride Catalog No.:AA01A16K CAS No.:1059626-08-2 MDL No.:MFCD09696855 MF:C8H10ClN3 MW:183.6381	4-(2-Phenyl-1H-imidazol-1-yl)butanoic acid hydrochloride Catalog No.:AA01FO4A CAS No.:1059626-15-1 MDL No.: MF:C13H15ClN2O2 MW:266.7234
N-Methyl-2-(2-methyl-1H-imidazol-1-yl)ethanamine dihydrochloride Catalog No.:AA00J15Z CAS No.:1059626-16-2 MDL No.:MFCD06801060 MF:C7H15Cl2N3 MW:212.1201	3-(2-Methyl-1H-imidazol-1-yl)propan-1-amine dihydrochloride Catalog No.:AA00J12O CAS No.:1059626-17-3 MDL No.:MFCD06801042 MF:C7H15Cl2N3 MW:212.1201
4-(2,3-dihydro-1H-indol-1-yl)butanoic acid hydrochloride Catalog No.:AA01B8E5 CAS No.:1059626-21-9 MDL No.:MFCD06800576 MF:C12H16ClNO2 MW:241.7139	6-Bromo-1h,2h,3h,4h,5h-pyrido[4,3-b]indole hydrochloride Catalog No.:AA019WNB CAS No.:1059630-11-3 MDL No.:MFCD12913162 MF:C11H12BrClN2 MW:287.5834
N-[(3-chlorophenyl)methyl]-N-methyl-3-oxobutanamide Catalog No.:AA019URX CAS No.:105964-54-3 MDL No.:MFCD09817252 MF:C12H14ClNO2 MW:239.6981	methyl 2-amino-2-(2,3-dihydro-1H-inden-1-yl)acetate Catalog No.:AA01EJG8 CAS No.:1059652-38-8 MDL No.:MFCD31666729 MF:C12H15NO2 MW:205.2530
N-Hydroxy-4-nitrophthalimide Catalog No.:AA003LTR CAS No.:105969-98-0 MDL No.:MFCD01115771 MF:C8H4N2O5 MW:208.1278	(1R)-1-(1-benzofuran-3-yl)ethan-1-ol Catalog No.:AA01B6EF CAS No.:1059698-12-2 MDL No.:MFCD24270490 MF:C10H10O2 MW:162.1852
4(7)-Nitrobenzimidazole Catalog No.:AA007W5R CAS No.:10597-52-1 MDL No.:MFCD00220143 MF:C7H5N3O2 MW:163.1335	3,4-Dihydroxyphenethyl alcohol Catalog No.:AA008QYP CAS No.:10597-60-1 MDL No.:MFCD01320529 MF:C8H10O3 MW:154.1632
N-Acetylmuramic acid Catalog No.:AA008RGC CAS No.:10597-89-4 MDL No.:MFCD00221511 MF:C11H19NO8 MW:293.2705	3-methyl-3,6-diazabicyclo[3.1.1]heptane; bis(trifluoroacetic acid) Catalog No.:AA00IKQU CAS No.:1059700-17-2 MDL No.:MFCD30802095 MF:C10H14F6N2O4 MW:340.2196
4-CYCLOHEXYLOXY-PHENYLAMINE HYDROCHLORIDE Catalog No.:AA0092G2 CAS No.:105971-50-4 MDL No.:MFCD11858349 MF:C12H18ClNO MW:227.7304	N-benzyl-5-methylpyridin-2-amine Catalog No.:AA009T2E CAS No.:105972-23-4 MDL No.:MFCD06637693 MF:C13H14N2 MW:198.2637
4-(2-Aminophenethyl)pyridine Catalog No.:AA008RL7 CAS No.:105972-24-5 MDL No.:MFCD04966953 MF:C13H14N2 MW:198.2637	1-Benzyl-3-piperidinol, HCl Catalog No.:AA003DXT CAS No.:105973-51-1 MDL No.:MFCD00044200 MF:C12H18ClNO MW:227.7304
Bms-833923 Catalog No.:AA008TBU CAS No.:1059734-66-5 MDL No.:MFCD25976660 MF:C30H27N5O MW:473.5683	7-Benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine Catalog No.:AA003868 CAS No.:1059735-34-0 MDL No.:MFCD11846183 MF:C14H13Cl2N3 MW:294.1791
tert-Butyl 7-aminoheptanoate Catalog No.:AA0084KK CAS No.:105974-64-9 MDL No.:MFCD12804784 MF:C11H23NO2 MW:201.3058	2-Amino-N-hydroxy-2-phenylacetamide Catalog No.:AA008VFZ CAS No.:105985-16-8 MDL No.:MFCD00243468 MF:C8H10N2O2 MW:166.1772
3-Chloropyrazin-2(1H)-one Catalog No.:AA009609 CAS No.:105985-17-9 MDL No.:MFCD18427098 MF:C4H3ClN2O MW:130.5324	5-Chloro-3-methyl-2(1h)-pyrazinone Catalog No.:AA0084KC CAS No.:105985-18-0 MDL No.:MFCD15144356 MF:C5H5ClN2O MW:144.5590
2-Chloro-5-(chloromethyl)pyrazine Catalog No.:AA0084KB CAS No.:105985-21-5 MDL No.:MFCD10697787 MF:C5H4Cl2N2 MW:163.0047	Ethyl 4-(4-bromophenyl)butanoate Catalog No.:AA007E6P CAS No.:105986-54-7 MDL No.:MFCD16037424 MF:C12H15BrO2 MW:271.1503
2-Isopropylfuran Catalog No.:AA003HF0 CAS No.:10599-59-4 MDL No.:MFCD10000651 MF:C7H10O MW:110.1537	2-Methyl-5-propionylfuran Catalog No.:AA00389F CAS No.:10599-69-6 MDL No.:MFCD00053142 MF:C8H10O2 MW:138.1638
1-(2,5-Dimethylfuran-3-yl)ethanone Catalog No.:AA003IQB CAS No.:10599-70-9 MDL No.:MFCD00010281 MF:C8H10O2 MW:138.1638	(S)-(-)-HigenaMine HydrobroMide Catalog No.:AA008W24 CAS No.:105990-27-0 MDL No.: MF:C16H18BrNO3 MW:352.2230
4-Bromo-1-methyl-3-phenyl-1H-pyrazole Catalog No.:AA007W5A CAS No.:105994-55-6 MDL No.:MFCD05664675 MF:C11H10N2O2 MW:202.2093	1-Methyl-3-phenyl-1H-pyrazole-4-carboxylic acid Catalog No.:AA0096ZH CAS No.:105994-56-7 MDL No.:MFCD05664673 MF:C11H10N2O2 MW:202.2093
1-Methyl-5-phenyl-1h-pyrazole-4-carboxylic acid Catalog No.:AA007E6K CAS No.:105994-75-0 MDL No.:MFCD04038957 MF:C11H10N2O2 MW:202.2093	4-Bromo-1-methyl-5-phenyl-1h-pyrazole Catalog No.:AA0038WX CAS No.:105994-77-2 MDL No.:MFCD04038958 MF:C10H9BrN2 MW:237.0959
2-Bromo-5-ethynylthiophene Catalog No.:AA0084K3 CAS No.:105995-73-1 MDL No.:MFCD08703509 MF:C6H3BrS MW:187.0570	Bis(2-methoxyethyl) adipate Catalog No.:AA003O63 CAS No.:106-00-3 MDL No.:MFCD00041905 MF:C12H22O6 MW:262.2995
Oxacyclohexadecan-2-one Catalog No.:AA003TI0 CAS No.:106-02-5 MDL No.:MFCD00039667 MF:C15H28O2 MW:240.3816	Octanoic acid,1,1'-[1,2-ethanediylbis(oxy-2,1-ethanediyl)] ester Catalog No.:AA0084B0 CAS No.:106-10-5 MDL No.:MFCD00048916 MF:C22H46O8 MW:438.5958
Octadecanoic acid, 2-(2-hydroxyethoxy)ethyl ester Catalog No.:AA007DL3 CAS No.:106-11-6 MDL No.:MFCD00045992 MF:C22H44O4 MW:372.5824	12-Hydroxyoctadecanoic acid Catalog No.:AA003AY5 CAS No.:106-14-9 MDL No.:MFCD00004592 MF:C18H36O3 MW:300.4766
Dipropyl adipate Catalog No.:AA003PNK CAS No.:106-19-4 MDL No.:MFCD00048696 MF:C12H22O4 MW:230.3007	6-Octen-1-ol, 3,7-dimethyl- Catalog No.:AA002TDA CAS No.:106-22-9 MDL No.:MFCD00002935 MF:C10H20O MW:156.2652
Geraniol Catalog No.:AA0033HC CAS No.:106-24-1 MDL No.:MFCD00002917 MF:C10H18O MW:154.2493	Nerol Catalog No.:AA0083Z2 CAS No.:106-25-2 MDL No.:MFCD00063204 MF:C10H18O MW:154.2493
(2E,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-ol Catalog No.:AA0035MR CAS No.:106-28-5 MDL No.:MFCD00002918 MF:C15H26O MW:222.3663	3,7-Dimethylocta-2,6-dien-1-yl butyrate Catalog No.:AA007D10 CAS No.:106-29-6 MDL No.:MFCD00036538 MF:C14H24O2 MW:224.3392
Butyric anhydride Catalog No.:AA003SSG CAS No.:106-31-0 MDL No.:MFCD00009389 MF:C8H14O3 MW:158.1950	Ethyl dodecanoate Catalog No.:AA003QCV CAS No.:106-33-2 MDL No.:MFCD00015065 MF:C14H28O2 MW:228.3709
Quinhydrone Catalog No.:AA0083QP CAS No.:106-34-3 MDL No.:MFCD00010310 MF:C12H10O4 MW:218.2054	3-Heptanone Catalog No.:AA003JFM CAS No.:106-35-4 MDL No.:MFCD00009483 MF:C7H14O MW:114.1855
1,4-Dibromobenzene Catalog No.:AA0032JX CAS No.:106-37-6 MDL No.:MFCD00000089 MF:C6H4Br2 MW:235.9040	4-Bromotoluene Catalog No.:AA0037X6 CAS No.:106-38-7 MDL No.:MFCD00000109 MF:C7H7Br MW:171.0345
4-Bromochlorobenzene Catalog No.:AA003KX2 CAS No.:106-39-8 MDL No.:MFCD00000600 MF:C6H4BrCl MW:191.4530	4-Bromoaniline Catalog No.:AA0038WM CAS No.:106-40-1 MDL No.:MFCD00007822 MF:C6H6BrN MW:172.0225
4-Bromophenol Catalog No.:AA00385T CAS No.:106-41-2 MDL No.:MFCD00002313 MF:C6H5BrO MW:173.0073	p-Xylene Catalog No.:AA0035GS CAS No.:106-42-3 MDL No.:MFCD00008556 MF:C8H10 MW:106.1650
4-Chlorotoluene Catalog No.:AA003L5V CAS No.:106-43-4 MDL No.:MFCD00000631 MF:C7H7Cl MW:126.5835	P-Cresol Catalog No.:AA003THH CAS No.:106-44-5 MDL No.:MFCD00191248 MF:C7H8O MW:108.1378
4-Methylbenzenethiol Catalog No.:AA0035GO CAS No.:106-45-6 MDL No.:MFCD00004851 MF:C7H8S MW:124.2034	1,4-Dichlorobenzene Catalog No.:AA0032K1 CAS No.:106-46-7 MDL No.:MFCD00000604 MF:C6H4Cl2 MW:147.0020
4-Chloroaniline Catalog No.:AA0033X0 CAS No.:106-47-8 MDL No.:MFCD00007835 MF:C6H6ClN MW:127.5715	4-Chlorophenol Catalog No.:AA0033XG CAS No.:106-48-9 MDL No.:MFCD00002318 MF:C6H5ClO MW:128.5563
P-Toluidine Catalog No.:AA0035GP CAS No.:106-49-0 MDL No.:MFCD00007906 MF:C7H9N MW:107.1531	P-Phenylenediamine Catalog No.:AA0032JQ CAS No.:106-50-3 MDL No.:MFCD00007901 MF:C6H8N2 MW:108.1411
1,4-Benzoquinone Catalog No.:AA009KJX CAS No.:106-51-4 MDL No.:MFCD00001591 MF:C6H4O2 MW:108.0948	4-Hydroxy-1-methylpiperidine Catalog No.:AA003T47 CAS No.:106-52-5 MDL No.:MFCD00006500 MF:C6H13NO MW:115.1735
4-Bromothiophenol Catalog No.:AA0033W2 CAS No.:106-53-6 MDL No.:MFCD00004845 MF:C6H5BrS MW:189.0729	4-Chlorothiophenol Catalog No.:AA0033XP CAS No.:106-54-7 MDL No.:MFCD00004847 MF:C6H5ClS MW:144.6219
2,5-Dimethylmorpholine Catalog No.:AA0092BY CAS No.:106-56-9 MDL No.:MFCD09971504 MF:C6H13NO MW:115.1735	Glycine anhydride Catalog No.:AA003QPK CAS No.:106-57-0 MDL No.:MFCD00006009 MF:C4H6N2O2 MW:114.1026
1，4-Dimethylpiperazine Catalog No.:AA00IKET CAS No.:106-58-1 MDL No.:MFCD00006156 MF:C6H14N2 MW:114.1888	2,3-Dihydroxypropyl acetate Catalog No.:AA003EGB CAS No.:106-61-6 MDL No.:MFCD00036185 MF:C5H10O4 MW:134.1305
Isobutyl acrylate Catalog No.:AA003QZS CAS No.:106-63-8 MDL No.:MFCD00042865 MF:C7H12O2 MW:128.1690	Dimethyl succinate Catalog No.:AA0034OK CAS No.:106-65-0 MDL No.:MFCD00008466 MF:C6H10O4 MW:146.1412
2-Ethyl-4-methylpentan-1-ol Catalog No.:AA00337V CAS No.:106-67-2 MDL No.:MFCD01709207 MF:C8H18O MW:130.2279	3-Octanone Catalog No.:AA003JRN CAS No.:106-68-3 MDL No.:MFCD00009515 MF:C8H16O MW:128.2120
1,2,6-Hexanetriol Catalog No.:AA003D8R CAS No.:106-69-4 MDL No.:MFCD00002976 MF:C6H14O3 MW:134.1736	Methyl Hexanoate Catalog No.:AA003RXO CAS No.:106-70-7 MDL No.:MFCD00009510 MF:C7H14O2 MW:130.1849
2-Cyanoethyl acrylate Catalog No.:AA003H1K CAS No.:106-71-8 MDL No.:MFCD00013823 MF:C6H7NO2 MW:125.1253	2,6-Dimethyl-5-heptenal Catalog No.:AA0037WI CAS No.:106-72-9 MDL No.:MFCD00006981 MF:C9H16O MW:140.2227
Dimethyl sebacate Catalog No.:AA003PJS CAS No.:106-79-6 MDL No.:MFCD00008472 MF:C12H22O4 MW:230.3007	2-Oxiraneoctanoic acid,3-octyl-, octyl ester Catalog No.:AA007BJ1 CAS No.:106-84-3 MDL No.:MFCD00214047 MF:C26H50O3 MW:410.6734
1,2-Epoxy-4-vinylcyclohexane Catalog No.:AA0082SM CAS No.:106-86-5 MDL No.:MFCD00022356 MF:C8H12O MW:124.1803	Vinylcyclohexene dioxide Catalog No.:AA00ILIM CAS No.:106-87-6 MDL No.:MFCD00022354 MF:C8H12O2 MW:140.1797
1,2-Epoxybutane Catalog No.:AA0082S6 CAS No.:106-88-7 MDL No.:MFCD00005153 MF:C4H8O MW:72.1057	2-Chloromethyl-oxirane Catalog No.:AA0039KS CAS No.:106-89-8 MDL No.:MFCD00005132 MF:C3H5ClO MW:92.5242
Glycidyl acrylate Catalog No.:AA008ULF CAS No.:106-90-1 MDL No.:MFCD00005138 MF:C6H8O3 MW:128.1259	Glycidyl methacrylate Catalog No.:AA003QPH CAS No.:106-91-2 MDL No.:MFCD00005137 MF:C7H10O3 MW:142.1525
1,2-Dibromoethane Catalog No.:AA0032HV CAS No.:106-93-4 MDL No.:MFCD00000233 MF:C2H4Br2 MW:187.8612	1-Bromopropane Catalog No.:AA0032NK CAS No.:106-94-5 MDL No.:MFCD00000254 MF:C3H7Br MW:122.9917
Allyl Bromide Catalog No.:AA0034D2 CAS No.:106-95-6 MDL No.:MFCD00000244 MF:C3H5Br MW:120.9758	3-Bromo-1-Propyne Catalog No.:AA0037W6 CAS No.:106-96-7 MDL No.:MFCD00000241 MF:C3H3Br MW:118.9599
1-Butene Catalog No.:AA003E36 CAS No.:106-98-9 MDL No.:MFCD00009383 MF:C4H8 MW:56.1063	1,3-Butadiene Catalog No.:AA003DFJ CAS No.:106-99-0 MDL No.:MFCD00008659 MF:C4H6 MW:54.0904
1,3-Bis[3,5-bis(trifluoromethyl)phenyl]thiourea Catalog No.:AA0032IK CAS No.:1060-92-0 MDL No.:MFCD00829878 MF:C17H8F12N2S MW:500.3047	N-(2-hydroxy-1,7-dimethyl-1H-indol-3-yl)acetamide Catalog No.:AA01BA3X CAS No.:106000-29-7 MDL No.:MFCD24590883 MF:C12H14N2O2 MW:218.2518
(6S)-2-Amino-6-propionamidotetrahydrobenzothiazole Catalog No.:AA007VZ2 CAS No.:106006-84-2 MDL No.:MFCD07369803 MF:C10H15N3OS MW:225.3106	(R)-N-(2-Amino-4,5,6,7-tetrahydro-benzothiazol-6-yl)-propionamide Catalog No.:AA0084JT CAS No.:106006-85-3 MDL No.:MFCD07369802 MF:C10H15N3OS MW:225.3106
2-[2-(ethylamino)ethoxy]ethan-1-ol Catalog No.:AA01B8K6 CAS No.:106007-99-2 MDL No.:MFCD11166432 MF:C6H15NO2 MW:133.1888	5,7-DICHLORO-1-METHYL-1H-INDOLE-2,3-DIONE Catalog No.:AA01AR43 CAS No.:106009-19-2 MDL No.:MFCD08755719 MF:C9H5Cl2NO2 MW:230.0475
5-Methoxy-3-formylindole Catalog No.:AA007VYT CAS No.:10601-19-1 MDL No.:MFCD00005623 MF:C10H9NO2 MW:175.1840	Propanamide, N-(1-methylethyl)- Catalog No.:AA01FN4M CAS No.:10601-63-5 MDL No.:MFCD03376407 MF:C6H13NO MW:115.1735
N-(3-Hydroxypropyl)acetamide Catalog No.:AA009REL CAS No.:10601-73-7 MDL No.:MFCD00178451 MF:C5H11NO2 MW:117.1463	Ethyl 3,3-diethoxypropionate Catalog No.:AA0035YE CAS No.:10601-80-6 MDL No.:MFCD00009865 MF:C9H18O4 MW:190.2368
3-Ethynylbenzoic acid Catalog No.:AA008RLY CAS No.:10601-99-7 MDL No.:MFCD06658448 MF:C9H6O2 MW:146.1427	(Z)-Hexadec-9-enamide Catalog No.:AA00389E CAS No.:106010-22-4 MDL No.:MFCD07374311 MF:C16H31NO MW:253.4234
1-(2-Amino-4-methylthiazol-5-yl)ethanone hydrochloride Catalog No.:AA019L3O CAS No.:106012-40-2 MDL No.:MFCD00159784 MF:C6H9ClN2OS MW:192.6665	Imidazo[1,2-a]pyrimidine-3-carbaldehyde Catalog No.:AA0037XL CAS No.:106012-56-0 MDL No.:MFCD09027563 MF:C7H5N3O MW:147.1341
Imidazo[1,2-a]pyrazine-3-carbaldehyde Catalog No.:AA0084JK CAS No.:106012-58-2 MDL No.:MFCD09027562 MF:C7H5N3O MW:147.1341	Dihydro-2,4-diMethyl-3(2H)-thiophenone Catalog No.:AA008X0F CAS No.:106014-15-7 MDL No.:MFCD24711320 MF:C6H10OS MW:130.2080
2,5-DiMethyl-3-thiaadipic Acid Catalog No.:AA008WLA CAS No.:106014-16-8 MDL No.:MFCD21109338 MF:C7H12O4S MW:192.2328	Dimethyl 3-chloropyridine-2,5-dicarboxylate Catalog No.:AA008YZK CAS No.:106014-21-5 MDL No.:MFCD00129113 MF:C9H8ClNO4 MW:229.6171
Rufloxacin hydrochloride Catalog No.:AA007E5Y CAS No.:106017-08-7 MDL No.:MFCD00912283 MF:C17H19ClFN3O3S MW:399.8675	2-(Trimethylsilyl)ethanesulfonyl chloride Catalog No.:AA0032T6 CAS No.:106018-85-3 MDL No.:MFCD09265153 MF:C5H13ClO2SSi MW:200.7590
4-Ethynylbenzoic acid Catalog No.:AA0035XV CAS No.:10602-00-3 MDL No.:MFCD00168819 MF:C9H6O2 MW:146.1427	2-(4-Bromophenyl)-1,3-dioxolane Catalog No.:AA003ESD CAS No.:10602-01-4 MDL No.:MFCD01318950 MF:C9H9BrO2 MW:229.0706
Ethyl 4-ethynylbenzoate Catalog No.:AA003Q7V CAS No.:10602-03-6 MDL No.:MFCD00168821 MF:C11H10O2 MW:174.1959	4-Ethynylbenzyl alcohol Catalog No.:AA003BSY CAS No.:10602-04-7 MDL No.:MFCD05664205 MF:C9H8O MW:132.1592
Methyl 3-ethynylbenzoate Catalog No.:AA0038WV CAS No.:10602-06-9 MDL No.:MFCD08703579 MF:C10H8O2 MW:160.1693	4,4-Diethoxybut-1-ene Catalog No.:AA003J2T CAS No.:10602-36-5 MDL No.:MFCD00012219 MF:C8H16O2 MW:144.2114