Copper-Catalyzed Synthesis of 2-Aminocarbazoles through Cascade C–C and C–N Bond Formation and Aromatization

Xinlei Liu, Jiangkun Huang, Huibei Xu, Dandan Zhang, Qiu Sun, and Ling He

 

Introduction
Carbazoles as structural motifs have been widely applied in ma- terial science such as organic electroluminescent materials,[1] organic photorefractive materials,[2] solar cell materials.[3] In ad- dition, carbazoles derivatives are also unique structural units in pharmaceuticals and natural products showing significant bio- logical activities. For example, staurosporine and its derivatives have a variety of biological activities[4] including antifungal, antihypertensive and antitumor. Moreover, carbazoles were also used in the dye industry and supramolecular recognition. Based on carbazoles  broad  application  and  their  importance (Scheme 1), it is of great significance to propose efficient meth- ods for the construction of carbazole derivatives with biological activity or specific function.[5]

Over the past decades, some general strategies for the syn- thesis of carbazoles have been developed.[6] These methods in- clude the formation of C–N/C–C bond and C–H cleavage (Scheme 2a), such as transition-metal-catalyzed intramolecular dehydrogenative cross-coupling, oxidative cyclization of diaryl- amines, transition metal free or rhodium catalyzed intramolec- ular C–H amination of anilides and nitrene insertion of 2-azidobiphenyls, and Pd catalyzed one-pot Suzuki-Cadogan cascade reaction of o-halonitrobenzenes. Although these methods are highly efficient and show good compatibility with functional groups, for the synthesis of multifarious carbazoles derivatives, they require the preparation of complex starting materials, such as amino-, azido-, nitro- and halo-substituted biaryls or indol-3- yl-3-yn-2-ols or N, N-biaryl amines or require expensive rea- gents. Therefore, we have exploited the development of a one- pot C–C/C–N bond formation and dehydrogenative tandem reaction that utilizes easily prepared starting materials with low cost and less toxic reagents. More recently, there are reports on the direct carbon-carbon coupling of indoles with alkenes and alkynes to provide carbazoles (Scheme 2b),[7] such as the syn- thesis of carbazoles via Pd-catalyzed and copper(II)-mediated reactions of indoles with in-situ generated aryl vinyl ketones using saturated ß-chloroalkyl aryl ketones as the olefins  source[7f] or the preparation of carbazoles via the Pd-catalyzed dehydrogenative cross-coupling of indoles with in situ gener- ated aryl vinyl ketones by using statured ketones as the olefins source under the presence of ligand PCy3, Ag2CO3, LiOAc, TEMPO, O2.[7g] However, the indole to carbazole transformation through direct cross-coupling using alkylketones are sparse in the literature. Especially, the direct intramolecular C–C coupling of indoles with alkanes has not been reported. Therefore, ongo- ing development of a greener and more concise procedure to acquire substituted carbazoles is still desirable.

 

To take advantage of easily preparable starting  materials  with a tolerance of most organic functional groups for the prep- aration of new pharmacologically active compounds, we devel- oped a copper-catalyzed oxidative cyclization based on easily available indole saturated side-chain ketones and inexpensive ammonium carbonate as nitrogen source, providing the novel 2-aminocarbazoles derivatives with moderate yields. This reac- tion completes the homogeneous cleavage of C–H bonds and the formation of C–C and C–N bonds in one pot reaction, by a sequence of free radical initiation, cyclization, Schiff base forma- tion, dehydrogenation, rearrangement and aromatization.

To initiate the study, the reaction using 1-(1H-indole-3-yl)- pentan-3-one (1a) as the model substrate and (NH4)2CO3 as nitrogen source was used to optimize the reaction conditions (Table 1). In order to evaluate the catalytic efficiency of various metal complexes including Yb(CF3SO3)3, Pd(OAc)2, Ru3(CO)12, (CpRhCl2)2, [Rh(CH3(CH2)6CO2)2]2, Cu(OAc)2, CuCl2, CuBr2, Cu(CF3SO3)2, the reaction of 1a with (NH4)2CO3 was studied by using a catalyst with acetonitrile as solvent at 80 °C. The results were shown in Table 1. It was found that only copper salts could be led to the formation of the desired carbazoles(3b) (Table 1, Entries 1- 14). Other metal complexes, such as Pd, Yb, and Rh, displayed poor catalytic activity (Entries 15- 18). At the same time, the catalytic effect of bivalent copper is generally better than that of univalent copper on this reaction. Among the cata- lysts of various copper salts, Cu(CF3SO3)2 was the most effective for the reaction (Table 1, entry 3). 

Since this reaction involves aromatization, so we also studied the effects of temperature, oxidants and solvents on the reac- tion yields, and the results are listed in Table  1.  Temperature also affected the reaction. At room temperature, the formation of carbazole was not observed. A further increase of tempera- ture (80–120 °C) led to the increase of reaction yields (Table 1, entries 3, 11, 13, 14). Meanwhile, the microwave irradiation has advantages of short reaction time over the traditional heating mode. But the yield was not obviously improved. Subsequently, we screened a series of oxidants to promote the aromatization via dehydrogenation process, such as PhI(OAc)2, I2, O2, NaIO4, Mn(OAc)3·2H2O, DDQ, etc, and it was found that these oxidants resulted in the formation of traces of carbazole products. How- ever, (E) 1- (1H-indol-3-yl) pent-1-en-3-one was obtained. And then the resulting trans-1- (1H-indol-3-yl)  pent-1-en-3-one  could not continue to cyclize and to form carbazoles under the same conditions. In addition, we investigated the solvent effect on the reaction. 1-(1H-indole-3-yl) pentan-3-one(1a) as model was heated in different solvents. Acetonitrile and methanol  were the most effective for the reaction, but the reaction hardly proceeded in xylene and decalin. The reaction carried out  in DMF and dimethylsulfoxide resulting in the formation of traces of carbazole under the same condition.

Furthermore, the influence of the nitrogen source on the  yield was studied, when other nitrogen sources such as (NH4)2C2O4, NH4Ac, etc. took the place of ammonium carb-  onate, no carbazole products were obtained. Other alkyl pri- mary amine and aromatic primary amine were tried as well, but the carbazole products were still not obtained. On the basis of these results, we used the optimum condition in a molar ratio    of 1a/ammonium carbonate/catalyst = 1.0:20:0.2 in acetonitrile at 80 °C for subsequent study.

 

After determining the optimum reaction conditions, in order to investigate the universality of the reaction, we investigated the substrate scope; the results are outlined in Scheme 3. A  series of 1-(1H-indole-3-yl)pentan-3-ones(R1 = H, R3 = Me, R4 =    H, Me, Ph) can successfully provide the corresponding carbazole products in moderate yields (the structure of 3e was confirmed by X-ray crystal structure CCDC 1589600) under identical condi- tions. Unfortunately, when a carbon chain was extended at the end of the indole side chain, the activity for the reactions was reduced under strictly identical conditions, such  as  3i,  3j,  3k, 3l, 3m(R3=Et). Meanwhile, we notice the substrate with the electron-donating substituent on the indole nitrogen (R1=Me) results in moderate yield, however, the substrate with the elec- tron-withdrawing groups on the indole nitrogen gave  only  trace amount of corresponding products, such as R1=Ph, Bn, Ts, Boc, Ac. The results showed that the reaction rate of indole changed with the presence of the protective groups on the nitrogen atom of indole.

CCDC 1589600 (for 3e) contains the supplementary crystallo- graphic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
To understand the observed reactivity, we investigated the reaction mechanism with deuterium-labeling experiments (Scheme 4). No significant kinetic isotope effect (KIE) was ob- served when the rate constants of the reaction of 1 and 1-D2 were measured, thus suggesting that C–H activation might not be involved in the rate-determining step (reaction 1, 2). In order to obtain more information about the reaction process, the rad- ical scavenger 2,2,6,6-tetra-methylpiperidino-oxy(TEMPO) was added to the original reaction system, the  products could  not be monitored completely under the same reaction conditions.

However, the peak of reactive intermediates could easily be de- tected from the reaction 3 (Scheme 4) by liquid chromatogra- phy-mass spectrometry, such as the peaks of m/z = 357.2, 355.2,
352.2. The reactive intermediates were captured by radical scav- engers, which suggests that the formation reaction of amino- carbazoles might go through a radical process. At the same  time, potassium carbonate, cesium carbonate, sodium tert-but- anol and DBU were employed as a reaction promoter. However, these bases have no obvious effect on the yield of the reaction. Thus, combined with our experimental results and the litera- tures,[8] we propose a possible reaction pathway for the forma- tion of 2-amonocarbazoles, as shown in Scheme 5. The 1-(1H-indol-3-yl)pentan-3-one was oxidized to give radi- cal intermediates by Cu(II), which recombined with side chain   to cyclize. Then the cyclic ketones were condensed with ammo- nia to give Schiff base. Finally, the double bonds occurred rear- rangement leading to aromatization and the formation of the 2-aminocarbazoles.

Conclusions
In summary, we report a simple and effective route to synthe- size 2-aminocarbazole derivatives by transition metal catalyzed conversion of indole side-chain ketones in a one-pot reaction with moderate yields. It uses easily made starting materials and many functional groups are tolerated. The indoles to carbazoles conversion protocol involves a cascade reaction with free radi- cal initiation, cyclization, condensation, dehydrogenation, rear- rangement and aromatization. Further studies of the scope, lim- itations and applications of this process are currently underway in our laboratory.

 

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3-CYANOPROPYLTRICHLOROSILANE Catalog No.:AA003J9P CAS No.:1071-27-8 MDL No.:MFCD00013832 MF:C4H6Cl3NSi MW:202.5416	3-Aminopropyl dihydrogen phosphate Catalog No.:AA0082IO CAS No.:1071-28-9 MDL No.:MFCD01757086 MF:C3H10NO4P MW:155.0896
(ethylsulfanyl)methanimidamide hydrobromide Catalog No.:AA003U61 CAS No.:1071-37-0 MDL No.:MFCD00012585 MF:C3H9BrN2S MW:185.0860	3-Ethoxy-3-oxopropanoic acid Catalog No.:AA003QCJ CAS No.:1071-46-1 MDL No.:MFCD00020490 MF:C5H8O4 MW:132.1146
3-Acetyl-1-propanol Catalog No.:AA00347H CAS No.:1071-73-4 MDL No.:MFCD00002961 MF:C5H10O2 MW:102.1317	Zirconium(IV) Tetrabutoxide Catalog No.:AA007T68 CAS No.:1071-76-7 MDL No.:MFCD00048765 MF:C16H36O4Zr MW:383.6786
2-[(phosphonomethyl)amino]acetic acid, 40% aqueous solution Catalog No.:AA0034WG CAS No.:1071-83-6 MDL No.:MFCD00055350 MF:C3H8NO5P MW:169.0731	Adipic dihydrazide Catalog No.:AA003QU1 CAS No.:1071-93-8 MDL No.:MFCD00007614 MF:C6H14N4O2 MW:174.2010
3-(Aminooxy)-1-propanethiol hydrochloride Catalog No.:AA008WX0 CAS No.:1071-99-4 MDL No.:MFCD15144903 MF:C3H10ClNOS MW:143.6356	5-Bromo-3,4-dimethylbenzene-1,2-diamine Catalog No.:AA007B30 CAS No.:107100-16-3 MDL No.:MFCD00052696 MF:C8H11BrN2 MW:215.0903
FKGK 11 Catalog No.:AA008SP2 CAS No.:1071000-98-0 MDL No.:MFCD18382097 MF:C13H13F5O MW:280.2337	2-Methyl-4,4,4-trifluorobutanol Catalog No.:AA0082IS CAS No.:107103-95-7 MDL No.:MFCD00190639 MF:C5H9F3O MW:142.1196
1-(4-Methylphenyl)-2,4,6-triphenylpyridinium tetrafluoroborate Catalog No.:AA01EQMA CAS No.:107108-26-9 MDL No.:MFCD00960926 MF:C30H24BF4N MW:485.3229	2-(2,2-dimethylcyclopropyl)ethan-1-ol Catalog No.:AA01CAAJ CAS No.:1071087-95-0 MDL No.:MFCD29971681 MF:C7H14O MW:114.1855
6,7-Dihydrothieno[3,2-C]-pyridine Catalog No.:AA008W7Q CAS No.:107112-93-6 MDL No.:MFCD30741464 MF:C7H7NS MW:137.2022	2-Hydroxy-4-(trifluoromethoxy)benzaldehyde Catalog No.:AA00HATX CAS No.:1071156-25-6 MDL No.:MFCD18397426 MF:C8H5F3O3 MW:206.1187
4-(2-chloro-6-fluorophenyl)-1H-1,2,3-triazole-5-carbonitrile Catalog No.:AA00ITI9 CAS No.:1071166-49-8 MDL No.:MFCD00245951 MF:C9H4ClFN4 MW:222.6063	Iloperidone-d3 Catalog No.:AA007B2Y CAS No.:1071167-49-1 MDL No.:MFCD30145898 MF:C24H25D3N2O4 MW:411.5086
Iloperidone-d3 Catalog No.:AA008WDG CAS No.:1071168-82-5 MDL No.: MF:C24H24D3FN2O4 MW:429.4991	1,4-diethyl-1,4,7-triazonane Catalog No.:AA01BU27 CAS No.:1071170-26-7 MDL No.:MFCD20683269 MF:C10H23N3 MW:185.3097
2,4-Xylidine-d6 Catalog No.:AA00962J CAS No.:1071170-27-8 MDL No.:MFCD22565800 MF:C8H5D6N MW:127.2166	3-Oxocyclobutyl pivalate Catalog No.:AA008ZRL CAS No.:1071194-23-4 MDL No.:MFCD24690600 MF:C9H14O3 MW:170.2057
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1-Benzhydrylazetidine Catalog No.:AA003DW4 CAS No.:107128-00-7 MDL No.:MFCD00192107 MF:C16H17N MW:223.3129	5-(4-Fluorophenyl)-1,2,4-triazin-3-amine Catalog No.:AA019X1L CAS No.:107128-47-2 MDL No.:MFCD06739746 MF:C9H7FN4 MW:190.1771
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Perindopril erbumine Catalog No.:AA00IKH7 CAS No.:107133-36-8 MDL No.:MFCD02313824 MF:C23H43N3O5 MW:441.6046	6-Methylbenzo[d]thiazole-2,4-diamine Catalog No.:AA008VBB CAS No.:1071346-94-5 MDL No.:MFCD11695879 MF:C8H9N3S MW:179.2422
3,6-dichlorobenzo[b]thiophene-2-carbonitrile Catalog No.:AA01BU8M CAS No.:1071350-10-1 MDL No.:MFCD11696309 MF:C9H3Cl2NS MW:228.0978	1-Cyclopentyl-1h-pyrrole-3-carbaldehyde Catalog No.:AA008V1F CAS No.:1071359-81-3 MDL No.:MFCD11695056 MF:C10H13NO MW:163.2163
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(3-Aminopropyl)dibenzylamine Catalog No.:AA00HAUL CAS No.:107142-94-9 MDL No.:MFCD12569920 MF:C17H22N2 MW:254.3700	Methyl 1-Methyl-1H-indazole-4-carboxylate Catalog No.:AA007B19 CAS No.:1071428-42-6 MDL No.:MFCD00509937 MF:C10H10N2O2 MW:190.1986
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N-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-β-D-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-heptadecanamide Catalog No.:AA01EPUS CAS No.:1071654-84-6 MDL No.: MF:C41H79NO11S MW:794.1311	2-(6-Oxopiperidin-2-yl)acetamide Catalog No.:AA01AJ5Y CAS No.:1071661-20-5 MDL No.:MFCD19382158 MF:C7H12N2O2 MW:156.1824
2-(1-Methyl-1h-imidazol-5-yl)acetic acid hydrochloride Catalog No.:AA01AF3X CAS No.:1071661-55-6 MDL No.:MFCD27500744 MF:C6H9ClN2O2 MW:176.6009	[(3-Methyl-2-thienyl)methyl]amine hydrochloride Catalog No.:AA00HAV0 CAS No.:1071674-80-0 MDL No.:MFCD09971550 MF:C6H10ClNS MW:163.6683
3,4-diethylaniline hydrochloride Catalog No.:AA01A4II CAS No.:1071678-12-0 MDL No.:MFCD18827535 MF:C10H16ClN MW:185.6937	N-[1-[2-(2-methylphenyl)ethyl]-4-piperidinyl]-N-phenyl-acetamide,monohydrochloride Catalog No.:AA01EQ9T CAS No.:1071703-90-6 MDL No.: MF:C22H29ClN2O MW:372.9315
N-(1-(4-Methylphenethyl)piperidin-4-yl)-N-phenylacetamideHydrochloride Catalog No.:AA01DZFI CAS No.:1071703-95-1 MDL No.:MFCD30186655 MF:C22H29ClN2O MW:372.9315	N-[1-[2-(4-methylphenyl)ethyl]-4-piperidinyl]-N-phenyl-propanamide,monohydrochloride Catalog No.:AA01EPP7 CAS No.:1071703-97-3 MDL No.: MF:C23H31ClN2O MW:386.9580
N-[1-[2-(3-methylphenyl)ethyl]-4-piperidinyl]-N-phenyl-acetamide,monohydrochloride Catalog No.:AA01EQ9P CAS No.:1071704-02-3 MDL No.: MF:C22H29ClN2O MW:372.9315	methyl 3-(2,4-dichlorophenoxy)propanoate Catalog No.:AA019Z2T CAS No.:1071715-08-6 MDL No.:MFCD00152418 MF:C10H10Cl2O3 MW:249.0906
(Z)-5H-Cyclopenta[b]pyridin-7(6h)-one o-methyl oxime Catalog No.:AA0096KM CAS No.:1071727-78-0 MDL No.:MFCD28975314 MF:C9H10N2O MW:162.1885	7-iodohept-1-ene Catalog No.:AA00KG7E CAS No.:107175-49-5 MDL No.:MFCD10570159 MF:C7H13I MW:224.0826
5H,6H,7H,8H,9H-cyclohepta[c]pyridin-3-amine Catalog No.:AA01DQQ9 CAS No.:1071763-80-8 MDL No.:MFCD22550643 MF:C10H14N2 MW:162.2316	6,7,8,9-Tetrahydro-5h-cyclohepta[d]pyrimidin-2-amine Catalog No.:AA00HAV3 CAS No.:1071763-85-3 MDL No.:MFCD18361690 MF:C9H13N3 MW:163.2196
2-(1,4-dimethyl-1H-pyrazol-5-yl)acetic acid Catalog No.:AA01EK33 CAS No.:1071814-38-4 MDL No.:MFCD20660111 MF:C7H10N2O2 MW:154.1665	(1-Methyl-1h-pyrazol-5-yl)acetonitrile Catalog No.:AA00397V CAS No.:1071814-43-1 MDL No.:MFCD09859321 MF:C6H7N3 MW:121.1399
2-(1-Methyl-1h-pyrazol-5-yl)acetic acid Catalog No.:AA0096FO CAS No.:1071814-44-2 MDL No.:MFCD18262290 MF:C6H8N2O2 MW:140.1399	(4-Phenyl-piperidin-4-ylmethyl)-carbamic acid tert-butyl ester Catalog No.:AA00HAV4 CAS No.:1071866-01-7 MDL No.:MFCD09753905 MF:C17H26N2O2 MW:290.4005
(S)-5-Bromo-N-((1-ethylpyrrolidin-2-yl)methyl)-2,3-dimethoxybenzamide Catalog No.:AA007T64 CAS No.:107188-74-9 MDL No.:MFCD00894744 MF:C16H23BrN2O3 MW:371.2694	FLB 457 Hydrobromide Catalog No.:AA007ARR CAS No.:107188-92-1 MDL No.:MFCD18252334 MF:C16H24Br2N2O3 MW:452.1814
2,4-Dichloro-5-nitrothiazole Catalog No.:AA009TAV CAS No.:107190-42-1 MDL No.:MFCD11131237 MF:C3Cl2N2O2S MW:199.0153	2-(3,5-Di-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Catalog No.:AA0094NL CAS No.:1071924-13-4 MDL No.:MFCD24039797 MF:C20H33BO2 MW:316.2858
Dl-dapoxetine hcl Catalog No.:AA008XLC CAS No.:1071929-03-7 MDL No.:MFCD20922882 MF:C21H24ClNO MW:341.8744	(5-(4-Fluorophenyl)thiophen-2-yl)(5-iodo-2-methylphenyl)methanone Catalog No.:AA00HAV5 CAS No.:1071929-08-2 MDL No.:MFCD12405594 MF:C18H12FIOS MW:422.2552
4-(4-Amino-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester Catalog No.:AA007T63 CAS No.:1071932-29-0 MDL No.:MFCD12026437 MF:C16H25N3O2 MW:291.3886	4-methoxy-3-(methoxycarbonyl)phenylboronic acid Catalog No.:AA00HAV6 CAS No.:1071958-96-7 MDL No.:MFCD23380361 MF:C9H11BO5 MW:209.9916
Benzyl 2-cyano-2-(4-fluoro-5-methyl-2-nitrophenyl)acetate Catalog No.:AA0096L1 CAS No.:1071974-01-0 MDL No.:MFCD28369447 MF:C17H13FN2O4 MW:328.2945	2-chloro-4-(propan-2-yloxy)aniline Catalog No.:AA01AG32 CAS No.:1071989-24-6 MDL No.:MFCD16680491 MF:C9H12ClNO MW:185.6507
AT406 Catalog No.:AA008WG6 CAS No.:1071992-99-8 MDL No.:MFCD22124467 MF:C32H43N5O4 MW:561.7149	1-(8-Azabicyclo[3.2.1]oct-3-yl)-2-methyl-1h-benzimidazole Catalog No.:AA00906Q CAS No.:1071993-26-4 MDL No.:MFCD08064258 MF:C15H19N3 MW:241.3315
6-(dimethylamino)hexanoic acid Catalog No.:AA01EK2X CAS No.:1072-09-9 MDL No.:MFCD20318750 MF:C8H17NO2 MW:159.2261	Silane, hexyl- Catalog No.:AA007T5T CAS No.:1072-14-6 MDL No.:MFCD00027291 MF:C6H16Si MW:116.2767
Adipaldehyde Catalog No.:AA008XJU CAS No.:1072-21-5 MDL No.:MFCD13186001 MF:C6H10O2 MW:114.1424	2-[(2-aminoethyl)disulfanyl]ethan-1-amine hydrochloride Catalog No.:AA01A7VY CAS No.:1072-22-6 MDL No.:MFCD06804621 MF:C4H13ClN2S2 MW:188.7424
Dodecyl isothiocyanate Catalog No.:AA003PSY CAS No.:1072-32-8 MDL No.:MFCD00041121 MF:C13H25NS MW:227.4093	Acetic acid tridecyl ester Catalog No.:AA003UYF CAS No.:1072-33-9 MDL No.:MFCD00056197 MF:C15H30O2 MW:242.3975
2,5,8,11,14,17,20-Heptaoxaheneicosane Catalog No.:AA0082C2 CAS No.:1072-40-8 MDL No.:MFCD00038357 MF:C14H30O7 MW:310.3838	4-Methyl-1,3-dioxolane Catalog No.:AA003LMM CAS No.:1072-47-5 MDL No.:MFCD00014109 MF:C4H8O2 MW:88.1051
1-Aziridineethanol Catalog No.:AA0038W6 CAS No.:1072-52-2 MDL No.:MFCD00005119 MF:C4H9NO MW:87.1204	Ethylenesulfate Catalog No.:AA0037VT CAS No.:1072-53-3 MDL No.:MFCD00221769 MF:C2H4O4S MW:124.1158
Cyclotetramethylenedimethylsilane Catalog No.:AA007T5B CAS No.:1072-54-4 MDL No.:MFCD00040240 MF:C6H14Si MW:114.2609	1-Methoxy-1-cyclopentene Catalog No.:AA009413 CAS No.:1072-59-9 MDL No.:MFCD30474836 MF:C6H10O MW:98.1430
1,3-Dioxolane,4-(chloromethyl)- Catalog No.:AA0082BV CAS No.:1072-61-3 MDL No.:MFCD02171168 MF:C4H7ClO2 MW:122.5502	2-Ethylimidazole Catalog No.:AA003B54 CAS No.:1072-62-4 MDL No.:MFCD00005192 MF:C5H8N2 MW:96.1304
1-Vinylimidazole Catalog No.:AA00HAV8 CAS No.:1072-63-5 MDL No.:MFCD00005297 MF:C5H6N2 MW:94.1145	3-Amino-5-methylisoxazole Catalog No.:AA003ITW CAS No.:1072-67-9 MDL No.:MFCD00003155 MF:C4H6N2O MW:98.1032
1,4-Dimethylpyrazole Catalog No.:AA003DM3 CAS No.:1072-68-0 MDL No.:MFCD01075158 MF:C5H8N2 MW:96.1304	5-Methyl-1,3-oxazolidin-2-one Catalog No.:AA007AQV CAS No.:1072-70-4 MDL No.:MFCD00068871 MF:C4H7NO2 MW:101.1039
1,3,4-Thiadiazolidine-2,5-dithione Catalog No.:AA00HAV9 CAS No.:1072-71-5 MDL No.:MFCD00003103 MF:C2H2N2S3 MW:150.2457	Tetrahydro-4H-thiopyran-4-one Catalog No.:AA003UMH CAS No.:1072-72-6 MDL No.:MFCD00006660 MF:C5H8OS MW:116.1814
3-Acetylpyrrole Catalog No.:AA0038W4 CAS No.:1072-82-8 MDL No.:MFCD00067759 MF:C6H7NO MW:109.1259	2-Acetylpyrrole Catalog No.:AA003G7Y CAS No.:1072-83-9 MDL No.:MFCD00005220 MF:C6H7NO MW:109.1259
1H-Imidazole-5-carboxylic acid Catalog No.:AA0032P2 CAS No.:1072-84-0 MDL No.:MFCD01365907 MF:C4H4N2O2 MW:112.0868	1-Bromo-2-fluorobenzene Catalog No.:AA00333Q CAS No.:1072-85-1 MDL No.:MFCD00000282 MF:C6H4BrF MW:174.9984
3-methylpyrrole-2,5-dione Catalog No.:AA009QTF CAS No.:1072-87-3 MDL No.:MFCD10699598 MF:C5H5NO2 MW:111.0987	4,5-Dimethyl-1,3-dihydro-2h-imidazol-2-one Catalog No.:AA007T4Y CAS No.:1072-89-5 MDL No.:MFCD00459895 MF:C5H8N2O MW:112.1298
1,3,5-Trimethyl-1H-pyrazole Catalog No.:AA003DDW CAS No.:1072-91-9 MDL No.:MFCD00015536 MF:C6H10N2 MW:110.1570	Ethyl-p-Methoxycinnamate Catalog No.:AA008RKP CAS No.:1072-93-1 MDL No.:MFCD01709801 MF:C5H7NOS MW:129.1802
Cyclohexane, (chloromethyl)- Catalog No.:AA007WFC CAS No.:1072-95-3 MDL No.:MFCD09908175 MF:C7H13Cl MW:132.6311	2-Amino-5-bromopyridine Catalog No.:AA00330T CAS No.:1072-97-5 MDL No.:MFCD00006323 MF:C5H5BrN2 MW:173.0106
2-Amino-5-chloropyridine Catalog No.:AA003310 CAS No.:1072-98-6 MDL No.:MFCD00006324 MF:C5H5ClN2 MW:128.5596	5-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-indole Catalog No.:AA0094QF CAS No.:1072009-08-5 MDL No.:MFCD16987816 MF:C14H17BFNO2 MW:261.0997
Benzyl n-methyl-n-(2-oxoethyl)carbamate Catalog No.:AA007T60 CAS No.:107201-33-2 MDL No.:MFCD14635609 MF:C11H13NO3 MW:207.2258	(R)-3-Aminotetrahydrofuran, HCl Catalog No.:AA0039BC CAS No.:1072015-52-1 MDL No.:MFCD08461720 MF:C4H10ClNO MW:123.5813
N-Boc-l-cyclohexylglycinol Catalog No.:AA003SR8 CAS No.:107202-39-1 MDL No.:MFCD04112591 MF:C13H25NO3 MW:243.3425	Erythro-n-boc-l-cyclohexylalanine epoxide Catalog No.:AA008R2J CAS No.:107202-62-0 MDL No.:MFCD08061628 MF:C15H27NO3 MW:269.3798
4-(4-Boc-1-piperazinyl)-5-bromo-7h-pyrrolo[2,3-d]pyrimidine Catalog No.:AA003JZG CAS No.:1072027-36-1 MDL No.:MFCD18642459 MF:C15H20BrN5O2 MW:382.2556	iridium(3+) ion bis(3,5-difluoro-2-(pyridin-2-yl)benzen-1-ide) 4-tert-butyl-2-(4-tert-butylpyridin-2-yl)pyridine hexafluoro-lambda5-phosphanuide Catalog No.:AA01EIFJ CAS No.:1072067-44-7 MDL No.:MFCD31657504 MF:C40H36F10IrN4P MW:985.9154
3-{3-carbamoyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-6-yl}propanoic acid Catalog No.:AA019UQC CAS No.:1072069-75-0 MDL No.:MFCD11857944 MF:C12H14N4O3 MW:262.2646	3-(2,3,3-trimethyl-3H-indol-5-yl)propanoic acid Catalog No.:AA00906R CAS No.:1072069-91-0 MDL No.:MFCD12922972 MF:C14H17NO2 MW:231.2903
6-Amino-5-methoxy-pyridine-2-carboxylic acid methyl ester Catalog No.:AA0093KM CAS No.:1072077-54-3 MDL No.:MFCD18261109 MF:C8H10N2O3 MW:182.1766	2-bromo-2-chloro-1,1-biphenyl Catalog No.:AA019EQZ CAS No.:107208-70-8 MDL No.:MFCD00466291 MF:C12H8BrCl MW:267.5489
5-Morpholinopicolinic acid Catalog No.:AA00995G CAS No.:1072103-29-7 MDL No.:MFCD18251373 MF:C10H12N2O3 MW:208.2139	(1R)-2-chloro-1-[4-(trifluoromethyl)phenyl]ethan-1-ol Catalog No.:AA01BCL2 CAS No.:1072105-58-8 MDL No.:MFCD24346567 MF:C9H8ClF3O MW:224.6074
3-(5-AMINO-3-METHYL-1H-1,2,4-TRIAZOL-1-YL)PROPANENITRILE Catalog No.:AA01EJML CAS No.:1072106-44-5 MDL No.:MFCD16845192 MF:C6H9N5 MW:151.1692	3-(5-amino-3-phenyl-1H-1,2,4-triazol-1-yl)propanenitrile Catalog No.:AA01EJQL CAS No.:1072106-46-7 MDL No.:MFCD24641918 MF:C11H11N5 MW:213.2385
2-METHYL-6H,7H-[1,2,4]TRIAZOLO[1,5-A]PYRIMIDIN-5-AMINE Catalog No.:AA01ELLE CAS No.:1072106-47-8 MDL No.:MFCD24641915 MF:C6H9N5 MW:151.1692	3-Iodo-5-nitropyridin-4-ol Catalog No.:AA008SAD CAS No.:1072140-97-6 MDL No.:MFCD11052833 MF:C5H3IN2O3 MW:265.9934
4-Chloro-1h-pyrrolo[2,3-b]pyridine-5-boronic acid pinacol ester Catalog No.:AA008U3S CAS No.:1072145-24-4 MDL No.:MFCD09965897 MF:C13H16BClN2O2 MW:278.5423	1,2-Difluoro-4-[2-[(trans,trans)-4'-propyl[1,1'-bicyclohexyl]-4-yl]ethyl]benzene Catalog No.:AA0094QB CAS No.:107215-66-7 MDL No.:MFCD28963786 MF:C23H34F2 MW:348.5129
Ethyl 2-(3-amino-2-hydroxyphenyl)acetate Catalog No.:AA01B8DM CAS No.:1072150-23-2 MDL No.:MFCD24642393 MF:C10H13NO3 MW:195.2151	5-Chloro-1-(triisopropylsilyl)-1h-pyrrolo[2,3-b]pyridine-4-boronic acid pinacol ester Catalog No.:AA007ARF CAS No.:1072152-34-1 MDL No.:MFCD09965900 MF:C22H36BClN2O2Si MW:434.8829
5-Bromo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrrolo[2,3-b]pyridine Catalog No.:AA0094GZ CAS No.:1072152-50-1 MDL No.:MFCD10574985 MF:C13H16BBrN2O2 MW:322.9933	rac3-Hydroxy-3-mercaptomethylquinuclidine Catalog No.:AA01DZFL CAS No.:107220-26-8 MDL No.:MFCD11042346 MF:C8H15NOS MW:173.2758
Cevimeline hydrochloride Catalog No.:AA007ARD CAS No.:107220-28-0 MDL No.:MFCD01961045 MF:C10H18ClNOS MW:235.7740	trans-CevimelineHydrochloride Catalog No.:AA01DZFM CAS No.:107220-29-1 MDL No.:MFCD01961046 MF:C10H18ClNOS MW:235.7740
Ethyl 4-fluoro-2-nitrobenzoate Catalog No.:AA009NXM CAS No.:1072207-10-3 MDL No.:MFCD10566267 MF:C9H8FNO4 MW:213.1625	(S,S)-1,3-Bis(4-bromobenzyl)-2-chlorooctahydro-2-(2E)-crotyl-1H-1,3,2-benzodiazasilole Catalog No.:AA003CM4 CAS No.:1072220-37-1 MDL No.:MFCD18632567 MF:C24H29Br2ClN2Si MW:568.8470
2-(3-Hydroxyphenoxy)acetonitrile Catalog No.:AA00HAVG CAS No.:107223-69-8 MDL No.:MFCD11181964 MF:C8H7NO2 MW:149.1467	3-Methyl-1H-pyrazolo[3,4-c]pyridine Catalog No.:AA0082CB CAS No.:1072249-89-8 MDL No.:MFCD13191779 MF:C7H7N3 MW:133.1506
3,6-Dichloro-4,5-diethylpyridazine Catalog No.:AA007AR7 CAS No.:107228-53-5 MDL No.:MFCD17014878 MF:C8H10Cl2N2 MW:205.0844	3,6-Dichloro-4-ethylpyridazine Catalog No.:AA0037VU CAS No.:107228-54-6 MDL No.:MFCD17014877 MF:C6H6Cl2N2 MW:177.0312
3,6-Dichloro-4-cyclobutylpyridazine Catalog No.:AA00HAVH CAS No.:107228-57-9 MDL No.:MFCD25955161 MF:C8H8Cl2N2 MW:203.0685	6-(4-Methoxyphenyl)hexanoic acid Catalog No.:AA01AA0M CAS No.:107228-87-5 MDL No.:MFCD12172613 MF:C13H18O3 MW:222.2802
2-Pyridinamine, 3-[(3-chlorophenyl)methoxy]- Catalog No.:AA0082C5 CAS No.:107229-62-9 MDL No.:MFCD11195108 MF:C12H11ClN2O MW:234.6815	3-(cyclohexylmethoxy)pyridin-2-amine Catalog No.:AA01A8DY CAS No.:107229-69-6 MDL No.:MFCD10689932 MF:C12H18N2O MW:206.2841
Cevimeline Catalog No.:AA0082C4 CAS No.:107233-08-9 MDL No.:MFCD22577792 MF:C10H17NOS MW:199.3131	1-(2-Chloropropanoyl)indoline Catalog No.:AA009PNU CAS No.:107236-27-1 MDL No.:MFCD05263162 MF:C11H12ClNO MW:209.6721
Zirconium 1,4-dicarboxybenzene MOF (UiO-66) Catalog No.:AA01FOVW CAS No.:1072413-89-8 MDL No.:MFCD29037163 MF:C48H24O32Zr6 MW:1660.0290	5-Iodo-1-methyl-1h-indazole Catalog No.:AA007AR0 CAS No.:1072433-59-0 MDL No.:MFCD11977535 MF:C8H7IN2 MW:258.0590
methyl 4-(aminomethyl)-3-fluorobenzoate hydrochloride Catalog No.:AA01B6DP CAS No.:1072438-51-7 MDL No.:MFCD17171306 MF:C9H11ClFNO2 MW:219.6405	Methyl 2-(aminomethyl)pyridine-4-carboxylate, HCl Catalog No.:AA007T5E CAS No.:1072438-54-0 MDL No.:MFCD09878665 MF:C8H11ClN2O2 MW:202.6381
Methyl 6-(aminomethyl)nicotinate hydrochloride Catalog No.:AA008ZD7 CAS No.:1072438-56-2 MDL No.:MFCD11045450 MF:C8H11ClN2O2 MW:202.6381	Methyl 3-amino-5-bromopicolinate Catalog No.:AA008U25 CAS No.:1072448-08-8 MDL No.:MFCD17015929 MF:C7H7BrN2O2 MW:231.0467
2-Amino-2-(3-methylphenyl)acetic acid HCl Catalog No.:AA0082C0 CAS No.:1072449-62-7 MDL No.:MFCD06410554 MF:C9H12ClNO2 MW:201.6501	1-(Dimethylamino)-6-methylheptan-3-one Catalog No.:AA00HAVI CAS No.:107245-26-1 MDL No.:MFCD22683883 MF:C10H21NO MW:171.2798
monoMETHACRYLOXYPROPYL FUNCTIONAL POLYTRIFLUOROPROPYLMETHYLSILOXANE, symmetric, 50-70 cSt Catalog No.:AA01EIBU CAS No.:1072456-00-8 MDL No.: MF: MW:	1-Fmoc-4-(hydroxymethyl)piperidine Catalog No.:AA00995K CAS No.:1072502-03-4 MDL No.:MFCD02094489 MF:C21H23NO3 MW:337.4122
5-Nitro-2-((3-phenylpropyl)amino)benzoic acid Catalog No.:AA00385A CAS No.:107254-86-4 MDL No.:MFCD00153851 MF:C16H16N2O4 MW:300.3092	4-[[3-[2-(3-Chlorophenyl)ethyl]-2-pyridinyl]carbonyl]-1-piperidinecarboxylic Acid Catalog No.:AA008W2U CAS No.:107256-32-6 MDL No.:MFCD16251304 MF:C22H25ClN2O3 MW:400.8985
Pk14105 Catalog No.:AA003TQE CAS No.:107257-28-3 MDL No.:MFCD28969041 MF:C21H20FN3O3 MW:381.4002	3-(1-(Boc-amino)ethyl)-pyrrolidine Catalog No.:AA00HAVK CAS No.:107258-90-2 MDL No.:MFCD18073167 MF:C11H22N2O2 MW:214.3046
Ethyl 1-(boc-amino)cyclopropanecarboxylate Catalog No.:AA003PXD CAS No.:107259-05-2 MDL No.:MFCD11845623 MF:C11H19NO4 MW:229.2729	(1-Formyl-cyclopropyl)-carbamic acid tert-butyl ester Catalog No.:AA0037VS CAS No.:107259-06-3 MDL No.:MFCD10697899 MF:C9H15NO3 MW:185.2203
1-(1-Benzylpyrrolidin-3-yl)ethanamine Catalog No.:AA01A52R CAS No.:107259-16-5 MDL No.:MFCD22057269 MF:C13H20N2 MW:204.3113	4-Ethynyl-2-methylthiazole Catalog No.:AA008U6X CAS No.:107263-89-8 MDL No.:MFCD18207414 MF:C6H5NS MW:123.1756
1-Fluoropyridinium Triflate Catalog No.:AA003AZ0 CAS No.:107263-95-6 MDL No.:MFCD00013458 MF:C6H5F4NO3S MW:247.1674	1-Fluoro-2,4,6-trimethylpyridin-1-ium trifluoromethanesulfonate Catalog No.:AA003E92 CAS No.:107264-00-6 MDL No.:MFCD00067525 MF:C9H11F4NO3S MW:289.2472
1-Fluoropyridinium tetrafluoroborate Catalog No.:AA003E9M CAS No.:107264-09-5 MDL No.:MFCD00153176 MF:C5H5BF5N MW:184.9029	ethyl 2-(2-amino-3-cyano-4,5-dimethyl-1H-pyrrol-1-yl)acetate Catalog No.:AA00IYYI CAS No.:107267-88-9 MDL No.:MFCD04126142 MF:C11H15N3O2 MW:221.2557
3-((2-Methylallyl)oxy)aniline Catalog No.:AA0082BS CAS No.:107268-37-1 MDL No.:MFCD06801092 MF:C10H13NO MW:163.2163	IFLAB-BB F1703-0109 Catalog No.:AA008X8V CAS No.:107269-65-8 MDL No.:MFCD06623794 MF:C8H10ClN5 MW:211.6515
(2-methyl-2H-1,2,3,4-tetrazol-5-yl)methanamine hydrochloride Catalog No.:AA01BFEC CAS No.:107269-68-1 MDL No.:MFCD28118594 MF:C3H8ClN5 MW:149.5821	N-(2,5-Diethoxyphenyl)-4-methyl-benzenesulfonamide Catalog No.:AA019EHW CAS No.:107276-46-0 MDL No.:MFCD10170348 MF:C17H21NO4S MW:335.4179
tert-Butyl n-[2-(oxiran-2-yl)ethyl]carbamate Catalog No.:AA01BCJZ CAS No.:1072793-83-9 MDL No.:MFCD24465622 MF:C9H17NO3 MW:187.2362	(2-Methylthiazol-5-yl)methanamine hydrochloride Catalog No.:AA00HAVO CAS No.:1072806-59-7 MDL No.:MFCD11506341 MF:C5H9ClN2S MW:164.6564
4-Oxazolemethanamine hydrochloride Catalog No.:AA0038W5 CAS No.:1072806-60-0 MDL No.:MFCD08437648 MF:C4H7ClN2O MW:134.5642	(2-Methylthiazol-4-yl)methanamine dihydrochloride Catalog No.:AA0092J6 CAS No.:1072806-63-3 MDL No.:MFCD11506341 MF:C5H10Cl2N2S MW:201.1173
1,3-Benzoxazol-2-ylmethylamine hydrochloride Catalog No.:AA008U23 CAS No.:1072806-65-5 MDL No.:MFCD09763577 MF:C8H9ClN2O MW:184.6229	2-(Aminomethyl)-1h-indole methanesulphonate Catalog No.:AA00982T CAS No.:1072806-66-6 MDL No.:MFCD03756929 MF:C10H14N2O3S MW:242.2948
4-Methoxyindole-2-boronic acid pinacol ester Catalog No.:AA007AQU CAS No.:1072811-21-2 MDL No.:MFCD11858387 MF:C15H20BNO3 MW:273.1352	4-Methylindole-2-boronic acid pinacol ester Catalog No.:AA0090CW CAS No.:1072811-23-4 MDL No.:MFCD11858397 MF:C15H20BNO2 MW:257.1358
4-Methoxycarbonylindole-2-boronic acid pinacol ester Catalog No.:AA007T51 CAS No.:1072811-67-6 MDL No.:MFCD11858381 MF:C16H20BNO4 MW:301.1453	2-(7-Methoxybenzofuran-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Catalog No.:AA00HAVU CAS No.:1072811-86-9 MDL No.:MFCD18383011 MF:C15H19BO4 MW:274.1200
7-Bromoindole-2-boronic acid pinacol ester Catalog No.:AA0090DA CAS No.:1072812-23-7 MDL No.:MFCD11858379 MF:C14H17BBrNO2 MW:322.0053	3-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-indole Catalog No.:AA0082BP CAS No.:1072812-35-1 MDL No.:MFCD16995768 MF:C15H20BNO2 MW:257.1358
[(1R)-1-{2-[(2,5-dichlorophenyl)formamido]acetamido}-3-methylbutyl]boronic acid Catalog No.:AA0037VR CAS No.:1072833-77-2 MDL No.:MFCD18251438 MF:C14H19BCl2N2O4 MW:361.0287	(S)-Fmoc-2-amino-2-methyl-succinic acid-4-tert-butyl ester Catalog No.:AA008Z6E CAS No.:1072845-47-6 MDL No.:MFCD12031692 MF:C24H27NO6 MW:425.4743
6-(2,2-Difluoroethoxy)pyridine-3-carboxylic acid Catalog No.:AA01A364 CAS No.:1072855-41-4 MDL No.:MFCD23701786 MF:C8H7F2NO3 MW:203.1429	6-((Tetrahydrofuran-3-yl)oxy)nicotinic acid Catalog No.:AA01FLYZ CAS No.:1072855-68-5 MDL No.:MFCD18259826 MF:C10H11NO4 MW:209.1986
ethyl 1-(aminomethyl)cyclopentane-1-carboxylate hydrochloride Catalog No.:AA01E7A0 CAS No.:1072856-85-9 MDL No.:MFCD30752272 MF:C9H18ClNO2 MW:207.6977	4-Isopropylquinazolin-2(1H)-one Catalog No.:AA019EKE CAS No.:107289-03-2 MDL No.:MFCD24559421 MF:C11H12N2O MW:188.2258
4-hydroxy-2,2-dimethylbutanenitrile Catalog No.:AA01B2LW CAS No.:107289-41-8 MDL No.:MFCD21185377 MF:C6H11NO MW:113.1576	1,3-Dimethyl-1H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione Catalog No.:AA00IWWL CAS No.:1072895-79-4 MDL No.:MFCD18157655 MF:C7H8N4O2 MW:180.1640
4,6-Dichloro-1,3-dimethyl-1h-pyrazolo[3,4-d]pyrimidine Catalog No.:AA008TZX CAS No.:1072895-86-3 MDL No.:MFCD11869749 MF:C7H6Cl2N4 MW:217.0553	Fmoc-3-amino-2-methylbenzoic acid Catalog No.:AA008RU0 CAS No.:1072901-47-3 MDL No.:MFCD01861304 MF:C23H19NO4 MW:373.4013
3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-methylbenzoic acid Catalog No.:AA008R2N CAS No.:1072901-59-7 MDL No.:MFCD01861379 MF:C23H19NO4 MW:373.4013	EthanaMine, 2-(5-broMo-2-nitrophenoxy)-N,N-diMethyl- Catalog No.:AA00995N CAS No.:1072906-04-7 MDL No.:MFCD11520820 MF:C10H13BrN2O3 MW:289.1258
4-Bromo-2-(2-(dimethylamino)ethoxy)aniline Catalog No.:AA01DLLX CAS No.:1072906-05-8 MDL No.:MFCD11520819 MF:C10H15BrN2O MW:259.1429	4H,6H,7H-Thieno[3,2-c]thiopyran-4-carboxylic acid Catalog No.:AA019SRC CAS No.:107292-02-4 MDL No.:MFCD20731128 MF:C8H8O2S2 MW:200.2779