2019-12-12 14:46:01
Alexey A. Festa, a Leonid G. Voskressensky a and Erik V. Van der Eycken
1. Introduction
Indole, indoline, oxindole and isatin scaffolds are present in numerous natural products, biologically active compounds, drugs and agrochemicals. This made the scientific community focus on the preparation and functionalization of these molecular entities through the whole history of organic synthesis. In the past few years green chemistry and sustainable development have evolved as main themes in new synthetic methodology design.
Since the seminal works of MacMillan,1 Yoon2 and Stephenson,3 the renewable resource of visible light to induce chemical transformations has drawn much attention due to its cheap, mild and practical nature. This review is dedicated to the emerging technique of visible light-mediated chemistry for the modification of indoles and related heterocycles.
As most of the organic compounds do not absorb visible light the use of photocatalysts (PC) is usually needed.4–8 The common PCs are based on Ru- or Ir-complexes or different organic dyes. The PC readily absorbs light and undergoes a transition from the ground (S0) to the singlet excited state (S1). Moreover, the best PCs usually have high probabilities for intersystem crossing to form a long-living triplet excited state (T1).
The T1 excited state usually mediates intermolecular processes, inducing further chemical transformations, most often based on single electron transfer (SET). The photoexcited PC becomes both a better oxidant and a better reducing agent, capable of either donating or accepting an electron. In general, mechanistic schemes may be depicted by a reductive quenching cycle (Scheme 1a) and an oxidative quenching cycle (Scheme 1b). In a reductive quenching cycle the photoexcited PC* acts as an oxidant first, taking an electron from an electron donor (ED), which is usually termed a reductive quencher. This generates a PC radical anion with a high reducing potential. The typical reductive quenchers are tertiary amines. Alternatively, the photoexcited PC* acts firstly as a reductant in an oxidative quenching
cycle, donating an electron to an electron acceptor (EA, oxidative quencher). This generates a PC+ radical cation with a higher oxidative potential than that of a PC*. The typical oxidative quenchers are polyhalomethanes, aryldiazonium salts, dicyanobenzenes, etc. Chemical transformations induced by energy transfer from the excited PC to substrate are also known. PC-free processes are also possible when one of the substrates itself is capable of absorbing light, or through the formation of a photoactive electron donor–acceptor (EDA) complex between the reactants.
2. Visible light-mediated functionalization of indoles
As the synthesis of indoles in general13 and under the action of visible light14 has been recently reviewed, we will not consider indole ring forming reactions in this review although several new examples of photocatalyzed reactions have appeared.
2.1. C–C bond forming reactions
2.1.1 Alkylation reactions. Alkylation of indoles may be achieved through free radical substitution with reactive species generated by SET from bromo-substituted diethylmalonate derivatives. Intramolecular alkylation was realized for the first time by Stephenson and co-workers, employing Ru(bpy)3Cl2 as a PC and NEt3 in DMF at room temperature under irradiation with visible light.18 The transformation of indole 1 afforded compound 2 in 60% yield along with reduced by-product .
Reductive quenching of photoexcited PC generates Ru(I)-species, able to reduce the C–Br bond, thus producing an electron deficient C-centred free radical 4. The free radical 4 readily undergoes a
cyclization on C(2) of the indole ring, and the aromatization completes the sequence (Scheme 2). The reaction works with variously substituted indoles, and even 5-membered rings may be formed.
The intermolecular reaction with bromomalonates was found to be unrealisable under the above-mentioned conditions due to the formation of dehalogenation products. The change of triethylamine to triarylamine prevented the reduction of free radicals through hydrogen atom transfer (HAT) processes. The use of 4-methoxy-N,N-diphenylaniline as a sacrificial reductive quencher was found to be the best to afford the desired coupling products 5 in a wide scope of indoles with moderate to excellent yields (Scheme 3).19 The C(2) selectivity of the process might be rationalized through the formation of a stable benzylic free radical 6. It is worth noting that the indole moiety in NH-Boc-protected Trp-Phe dipeptide may be functionalized by the developed procedure.
The employment of the more strongly reducing Ir(III)-catalyst enables direct alkylation of an indole with tertiary bromomalonates without use of a reductive quencher.20 The reaction between indole and bromomalonate is carried out in acetonitrile at rt in the presence of Ir(ppy)3 and 2,6-lutidine under irradiation with blue LEDs. The reaction works well for indoles with different substitution patterns, containing halogen, alkyl or hydroxyl groups, with most of the examples made with N-unsubstituted indoles. When indole-2-carboxylate is used, the alkylation occurs at the C(3) position. The reaction also
worked smoothly with various bromomalonates, including N-Bocpiperidin-4-yl or allyl-substituted ones, though the interaction of a seven-membered bromolactone and a mixed malonate demanded the use of 20 equiv. of indole to obtain moderate yields.
The transformation was also tested under continuous flow conditions giving an improved reaction time and the possibility of generating the target product 7 with a conversion rate of 1.0 mmol per hour (Scheme 4). The use of an Ir(III)-catalyst also allows direct cyanomethylation of the indole ring through an oxidative quenching cycle. A photoexcited [Ir(dmppy)2(dtbbpy)]PF6 complex is capable of donating an electron to bromoacetonitrile to form a bromide anion and a cyanomethyl free radical. Irradiating 1-methylindole and bromoacetonitrile solution in DCE with a blue LED in the presence of the Ir(III) catalyst and NaHCO3 at room temperature results in the formation of 2-cyanomethylindoles 8. Better yields were obtained for N-protected indoles, giving rise to a wide scope of products. The procedure was shown to be inappropriate for C(2)-cyanomethylation of 5-azaindole or 3-pyridoindole due to the formation of quaternary salts (Scheme 5). If the C(2)-position was blocked with a substituent, the alkylation took place at C(3).
Photoinduced generation of (phenylsulfonyl)methyl free radicals has been developed and employed for indole alkylation by Li and a co-worker.22 The reaction of indole and bromomethyl phenyl sulfone 9 in DMSO in the presence of Li2CO3 and Ir(ppy)3 under irradiation with a household 14 W light bulb indeed gives the C(2)-(phenylsulfonyl)methylated product 10 (Scheme 6). The photoexcited Ir(III)* PC reduces bromomethyl phenyl sulfone 9 to produce a (phenylsulfonyl)methyl free radical, which attacks an indole. The recyclation of the catalyst occurs through oxidation of the indolyl radical by Ir(IV). The reaction has been mostly studied on pyrroles, but both N-unsubstituted indole and N-methylindole give the corresponding products.
Previously, an elegant indirect two-step methylation of heteroarenes has been realized by Baran et al., 23 who prepared the (phenylsulfonyl)methylated intermediates in a first step. Zinc bis(phenylsulfonylmethanesulfinate) was synthesized initially from the bromomethyl phenyl sulfones 9. As stoichiometric amounts of zinc and an additional synthetic step were needed work as photocatalysts for the trifluoromethylation reaction.
Another possible source of trifluoromethyl free radicals was Togni’s reagent, which was successfully used for indole trifluoromethylation with methylene blue as a photosensitizer. C(3) alkylation of indole is possible when imine or iminium intermediates are involved. In 2012 Stephenson and co-workers realized an amidoalkylation of electron-rich aromatic compounds with dialkylamides under photoredox conditions with Ru(bpy)3Cl2 as a catalyst. Indoles can also be used in the reaction with DMF as a reagent; though N-unsubstituted indole works poorly, N-phenyl and N-benzyl derivatives 13 can be obtained with moderate yields.
The formation of the iminium intermediate 14 is rationalized by the initial reduction of persulfate with photoexcited Ru(II)*. The formed sulfate radical anion abstracts a H-atom from DMF to give an a-amido radical 15, which is subsequently oxidized by either the Ru(III) PC or persulfate (Scheme 9).
Analogous generation of reactive imines has been realized by Li and co-workers, who have reported a mild method for the construction of 2-(1H-indol-3-yl)-2-aminocarbonyl compounds 16 by the reaction of indoles with a-amino carbonyl compounds 17 under visible light photoredox catalysis (Scheme 10).31 In this case, the formation of reactive iminium intermediates is explained by the initial single electron oxidation of amine 17 by photoexcited Ru(II)-species.
An interesting continuation of this work has been given by Zhang and co-workers, who developed a visible light-induced aerobic double Friedel–Crafts alkylation reaction of glycine derivatives and indole to access 3,30-bisindolylmethanes. The reaction proceeds in the presence of the photocatalyst rhodamine-G and citric acid in DCE at room temperature via a similar process, but the originally formed alkylation product undergoes single electron oxidation, iminium ion formation and Friedel–Crafts alkylation to form the target bisindolylmethane derivatives 18 in 95% yield (Scheme 11). The reaction has been investigated with various ester groups in substrate 17, such as methyl ester, isopropyl ester, t-butyl ester, allyl ester, and benzyl ester and different substituents at the benzene ring, showing very good tolerance. N-Protected indoles and benzene ring substituted indoles show moderate to good yields under optimized conditions, whereas indoles with strong electron withdrawing groups like Boc at the nitrogen atom fail to give any product. Citric acid is assumed to promote the second alkylation step.
Dihydroisoquinolinium salts may be generated in situ under photoredox catalysis conditions and used for indole alkylation. Firstly, platinum(II) terpyridyl complex 19 has been used for visible light-induced single electron oxidation of N-aryltetrahydroisoquinolines with further oxidation by a superoxide anion radical and trapping of the resulting iminium ion with indole to give products 20 in 56–81% yields (Scheme 12).
Addition of iron(II) sulphate is needed to neutralize the formed hydroperoxides and prevent their interaction with the isoquinoline free radical.33 Secondly, the same transformation has been realized without the need for air or stoichiometric amounts of iron.34 In this case, the catalytic system of Eosin Y with a graphene-supported RuO2 nanocomposite (G-RuO2) has been used, and hydrogen was extruded from the reaction mixture as molecular hydrogen H2.
Valuable 3,30-bisindolylmethanes 21 are prepared through a photocatalytic sequential alkylation of indoles with ethers or alcohols.35 Aryldiazonium salt works as an oxidative quencher of the PC’s excited state, and the aryl radical also abstracts a hydrogen from the ether to generate a reactive free radical 22, which, in turn, attacks the indole to form intermediate 23. The SET oxidation of 23 by Ru(III), followed by aromatization with a loss of proton, results in monoindolylated compound 24.
The formation of the desired bisindolylmethane 21 is explained by proton-promoted Friedel–Crafts alkylation of 24 with another equivalent of indole (Scheme 13). An interesting example of indole C(3) benzylation has been discovered by He and co-workers.36 Under the action of Rose Bengal, visible light, and air, indole and dimethyl aniline 25 are found to form 3-arylmethylindoles 26 (Scheme 14). The benzylic CH2 originates from dimethylaniline, taken in excess. Mechanistic investigations showed that energy transfer or photoredox catalysis pathways are both viable. Later, it has been suggested that
dimethylaniline undergoes demethylation and formaldehyde release, which could react with indole to produce an indolyl cation, capable of reacting with another molecule of dimethylaniline to give benzylated products 26.
Although the scope is not very wide from the viewpoint of dimethylaniline, the reaction tolerates N-unsubstituted indoles, with different groups in the benzene ring. Some problems with alkylation of indoles with halides have also been reported, in general stating that in the case of indoles with electron-withdrawing groups at C(3) (EWG = CN, CO2R), the alkylation proceeds without rearomatization of the indole
nucleus, and dearomatized products are predominantly formed. These examples are discussed further in Section 2.6 Dearomatization reactions.
In general, it can be concluded that the alkylation of indoles with free radical species occurs mainly at C(2) due to a better stability of the formed benzylic free radical. When N-acyl, benzoyl or aryl indoles are employed, the free radical substitution occurs at the C(3)-position. The alkylation with common electrophilic species like iminium ions expectedly gives C(3)-alkylated products.
Carbonylation reactions. Li and co-workers have reported a visible light-mediated C(3)-formylation of indoles with Rose Bengal used as a catalyst.38 The reaction is carried out in an MeCN–water mixture with potassium iodide as an additive, TMEDA 17 as a one carbon source and oxygen as a terminal oxidant. A wide scope of indoles may be formylated with moderate to good yields, though – not unexpectedly – N-protection with electron withdrawing groups (N-Boc, N-Ts) gives only trace amounts of product 18. The reaction proceeds through initial iminium salt formation and indole alkylation to provide intermediate 29. Its oxidation results in the formation of iminium salt 30, which is hydrolysed to complete the sequence (Scheme 15). A series of carbazole-based conjugated microporous polymers have been recently synthesized, and their utility for C(3) formylation of indoles instead of Rose Bengal has been realized with TMEDA as a carbonyl source.
Van der Eycken, Noe¨l and co-workers have reported a combined visible light photoredox catalysis and transition metal-catalyzed C–H activation for the C(2) acylation of N-pyrimidyl indole 31 with various aldehydes in the presence of a fac-[Ir(ppy)3] photocatalyst, Pd(OAc)2, TBHP and protected amino acid in acetonitrile at room temperature to afford acylated products 32.
The photocatalytic reduction of t-BuOOH by Ir(III)* leads to the formation of t-BuO radicals, able to abstract a hydrogen atom from an aldehyde to give acyl radical 33. Meanwhile, Pd(II) forms a palladacycle 34, which traps the acyl radical 33 to form intermediate 35. The oxidation of Pd(III) in intermediate 35 by Ir(IV) completes the photocatalytic cycle. The recyclation of Pd(II) is achieved via reductive elimination from compound 36. The reaction has been investigated in batch and continuous flow. The yields are good for both methods, but the reaction under continuous flow conditions requires less time and a lower catalyst loading. Noteworthily, the reaction works nicely with heteroaromatic and aliphatic aldehydes (Scheme 16).
A different carbonylation strategy uses CO gas and a source of aryl radical. For instance, interaction of aryldiazonium tetrafluoroborates, indole, and CO (70 atm) in an autoclave with a quartz window, in the presence of Eosin Y (1 mol%) and under irradiation with visible light gives C(3)-acylated products 37.
The reaction goes smoothly regardless of the substituent in indole or aryldiazonium salt, except for ortho-substituted aryldiazoniums which gave slightly lower yields, pointing to the steric dependence of the process. It has been shown that sulfonyl chlorides might also be used as aryl radical precursors.42 In both cases, the reactions start with photoexcited PC* reducing the aryldiazonium salt or sulfonyl chloride. It leads to the extrusion of N2 or SO2, respectively, to give an aryl radical, able to react with CO, producing an acyl radical. The single electron oxidation of the acyl radical by PC+ presumably gave an acylium ion, which finally reacted with an indole to give the target product 37 (Scheme 17).
Carboxylation reaction. Indole-2-carboxylates are derivatives of high demand, present in natural products and valuable for future modifications. Introduction of this moiety should be planned either at the step of indole cyclization or in the very beginning of the synthetic sequence due to the use of aggressive reagents (organolithium compounds). A direct and benign carboxylation has been developed by Bandini, Ceroni, and co-workers.43 In a typical experiment, an indole and CBr4 with diisopropylamine have been irradiated in MeOH at rt in the presence of a Ru(II) PC. Oxidative quenching of the photoexcited PC* with CBr4 generated a CBr3 free radical, which is trapped by the indole. Further rearomatization and methanolysis of the CBr3 group led to the formation of target indole-carboxylate 38
(Scheme 18). The reaction scope is wide, and even substrates with amine, propargylamine, and allylamine moieties are smoothly carboxylated. It is worth noting, that when R2 = H, the carboxylation occurs at the C(3) position, except for 4-bromo substituted indoles, which are carboxymethylated at C(2).
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4-(Chloromethyl)-5-methyl-2-phenyloxazoleCatalog No.:AA008SLG CAS No.:103788-61-0 MDL No.:MFCD00800940 MF:C11H10ClNO MW:207.6562 |
4,7-Dichloro-1,3-dihydro-3-hydroxy-3-[2-(4-methoxyphenyl)-2-oxoethyl]-2H-indol-2-oneCatalog No.:AA008SO1 CAS No.:1037184-44-3 MDL No.:MFCD18382120 MF:C17H13Cl2NO4 MW:366.1954 |
Diethanolamine-D8Catalog No.:AA008SXT CAS No.:103691-51-6 MDL No.:MFCD01317440 MF:C4H3D8NO2 MW:113.1849 |
5-Amino-2-phenyl-2H-1,2,3-triazole-4-carboxamideCatalog No.:AA008T0B CAS No.:103752-72-3 MDL No.:MFCD02218166 MF:C9H9N5O MW:203.2007 |
2-Ethylcyclobutan-1-oneCatalog No.:AA008T5F CAS No.:10374-14-8 MDL No.:MFCD00049150 MF:C6H10O MW:98.1430 |
5-Ethyl-2-[4-[4-[[4-(1H-tetrazol-1-yl)phenoxy]methyl]-2-thiazolyl]-1-piperidinyl]pyrimidineCatalog No.:AA008TEY CAS No.:1037792-44-1 MDL No.:MFCD22628771 MF:C22H24N8OS MW:448.5440 |
1-(6,7-Dihydro-5H-benzo[6,7]cyclohepta[1,2-c]pyridazin-3-yl)-N3-[(7S)-6,7,8,9-tetrahydro-7-(1-pyrrolidinyl)-5H-benzocyclohepten-2-yl]-1H-1,2,4-triazole-3,5-diamineCatalog No.:AA008TGI CAS No.:1037624-75-1 MDL No.:MFCD21608463 MF:C30H34N8 MW:506.6446 |
(S)-1-(4-(Methylsulfonyl)phenyl)ethanamineCatalog No.:AA008TLR CAS No.:1037798-64-3 MDL No.:MFCD06761968 MF:C9H13NO2S MW:199.2700 |
MiboplatinCatalog No.:AA008TN0 CAS No.:103775-75-3 MDL No.:MFCD00866309 MF:C11H18N2O4Pt MW:437.3496 |
Methyl 2-chloroquinazoline-6-carboxylateCatalog No.:AA008TU2 CAS No.:1036755-96-0 MDL No.:MFCD17016011 MF:C10H7ClN2O2 MW:222.6278 |
(1H-Pyrazol-5-yl)methanamine dihydrochlorideCatalog No.:AA008UBL CAS No.:1037237-32-3 MDL No.:MFCD12545920 MF:C4H9Cl2N3 MW:170.0404 |
2-(3-propoxyphenyl)ethan-1-amineCatalog No.:AA008V5C CAS No.:103686-13-1 MDL No.:MFCD08449852 MF:C11H17NO MW:179.2588 |
5-(2-Acetoxyethyl)-3-((4-amino-2-methylpyrimidin-5-yl)methyl)-4-methylthiazol-3-ium chloride hydrochlorideCatalog No.:AA008VPE CAS No.:1037-29-2 MDL No.:MFCD00210717 MF:C14H20Cl2N4O2S MW:379.3052 |
Methyl 3-(benzyloxy)-4-hydroxybenzoateCatalog No.:AA008WOO CAS No.:1037072-57-3 MDL No.:MFCD23110745 MF:C15H14O4 MW:258.2693 |
MoexiprilatCatalog No.:AA008WRU CAS No.:103775-14-0 MDL No.:MFCD08063675 MF:C25H30N2O7 MW:470.5149 |
Methyl 2,4-dioxo-4-(o-tolyl)butanoateCatalog No.:AA008X8X CAS No.:1037130-77-0 MDL No.:MFCD11188866 MF:C12H12O4 MW:220.2213 |
2-Bromo-5-chloro-1,3-dimethylbenzeneCatalog No.:AA008XMY CAS No.:103724-99-8 MDL No.:MFCD07780649 MF:C8H8BrCl MW:219.5061 |
H-D-Tic-Otbu HClCatalog No.:AA008Y3P CAS No.:103733-29-5 MDL No.:MFCD00672372 MF:C14H20ClNO2 MW:269.7671 |
6-Azaspiro[2.5]octane hydrochlorideCatalog No.:AA008YZH CAS No.:1037834-62-0 MDL No.:MFCD18838830 MF:C7H14ClN MW:147.6458 |
Tetrasodium Ethylenediaminetetraacetate DihydrateCatalog No.:AA008Z3V CAS No.:10378-23-1 MDL No.:MFCD00012460 MF:C10H16N2Na4O10 MW:416.2005 |
Methyl 3-(4-nitrophenoxy)thiophene-2-carboxylateCatalog No.:AA008ZF6 CAS No.:103790-37-0 MDL No.:MFCD00202717 MF:C12H9NO5S MW:279.2686 |
O-[(5-Amino-2-phenyl-7-benzoxazolyl)methyl]-3,5-dichloro-L-tyrosineCatalog No.:AA008ZS6 CAS No.:1037592-40-7 MDL No.:MFCD30534398 MF:C23H19Cl2N3O4 MW:472.3207 |
3-aminopropylphosphinic acidCatalog No.:AA008ZYD CAS No.:103680-47-3 MDL No.:MFCD05662182 MF:C3H10NO2P MW:123.0908 |
Morpholino(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanoneCatalog No.:AA00904Q CAS No.:1036991-25-9 MDL No.:MFCD09266172 MF:C17H24BNO4 MW:317.1878 |
1-(Imidazo[1,2-a]pyridin-7-yl)ethanoneCatalog No.:AA0091DJ CAS No.:1036991-50-0 MDL No.:MFCD20527734 MF:C9H8N2O MW:160.1726 |
(2S,2'S)-1,1'-(2,2'-((3-Hydroxyadamantan-1-yl)azanediyl)bis(acetyl))bis(pyrrolidine-2-carbonitrile)Catalog No.:AA0091TZ CAS No.:1036959-23-5 MDL No.:MFCD29127463 MF:C24H33N5O3 MW:439.5505 |
tert-Butyl N-{1-[(3-methoxypropyl)carbamoyl]ethyl}carbamateCatalog No.:AA009445 CAS No.:1037073-41-8 MDL No.:MFCD22549328 MF:C12H24N2O4 MW:260.3300 |
methyl 2-amino-4-fluoro-5-methylbenzoateCatalog No.:AA0095BB CAS No.:1037206-86-2 MDL No.:MFCD20691241 MF:C9H10FNO2 MW:183.1796 |
(4-(Pyrrolidin-1-ylmethyl)phenyl)boronic acidCatalog No.:AA0095HM CAS No.:1036991-20-4 MDL No.:MFCD06801708 MF:C11H16BNO2 MW:205.0612 |
(2R)-VildagliptinCatalog No.:AA0095JE CAS No.:1036959-27-9 MDL No.:MFCD13250201 MF:C17H25N3O2 MW:303.3993 |
(3-Iodoimidazo[1,2-a]pyridin-7-yl)methanolCatalog No.:AA0095ND CAS No.:1036990-66-5 MDL No.:MFCD12400829 MF:C8H7IN2O MW:274.0585 |
2-Amino-4-fluoro-5-methylbenzonitrileCatalog No.:AA0095UB CAS No.:1037206-84-0 MDL No.:MFCD16658717 MF:C8H7FN2 MW:150.1530 |
Benzyl 6-azaspiro[2.5]octane-6-carboxylateCatalog No.:AA0096DU CAS No.:1037834-61-9 MDL No.:MFCD18910975 MF:C15H19NO2 MW:245.3169 |
2-Amino-4,5-dibromophenolCatalog No.:AA0096KP CAS No.:1037298-16-0 MDL No.:MFCD26401820 MF:C6H5Br2NO MW:266.9180 |
tert-Butyl 4-[2-amino-4-(methoxycarbonyl)-phenylamino]piperidine-1-carboxylateCatalog No.:AA0096SS CAS No.:1037833-90-1 MDL No.:MFCD11974917 MF:C18H27N3O4 MW:349.4247 |
6-Amino-3-bromo-2-fluorobenzoic acidCatalog No.:AA0096WA CAS No.:1036756-03-2 MDL No.:MFCD20482512 MF:C7H5BrFNO2 MW:234.0225 |
2-Amino-5-chloro-4-iodophenolCatalog No.:AA00972X CAS No.:1037298-24-0 MDL No.:MFCD27978469 MF:C6H5ClINO MW:269.4675 |
5-(4-Hydroxybenzylidene)thiazolidine-2,4-dioneCatalog No.:AA009742 CAS No.:103788-60-9 MDL No.:MFCD00640639 MF:C10H7NO3S MW:221.2325 |
2-[(2-Aminophenyl)(methyl)amino]ethanolCatalog No.:AA0097ZK CAS No.:103763-87-7 MDL No.:MFCD11642970 MF:C9H14N2O MW:166.2203 |
tert-butyl 3-carbamothioylazetidine-1-carboxylateCatalog No.:AA00992E CAS No.:1037798-36-9 MDL No.:MFCD18910973 MF:C9H16N2O2S MW:216.3005 |
6-Bromo-2-chloro-5-fluoroquinazolineCatalog No.:AA009LQZ CAS No.:1036756-07-6 MDL No.:MFCD16250427 MF:C8H3BrClFN2 MW:261.4782 |
2'-Bromo-5'-phenyl-1,1':3',1''-terphenylCatalog No.:AA009LVO CAS No.:10368-73-7 MDL No.:MFCD00092320 MF:C24H17Br MW:385.2958 |
5-chloro-1-methyl-1H-1,3-benzodiazol-2-amineCatalog No.:AA009P5A CAS No.:103748-25-0 MDL No.:MFCD01658290 MF:C8H8ClN3 MW:181.6222 |
1-(aminomethyl)-2,3-dihydro-1H-inden-1-olCatalog No.:AA009PNQ CAS No.:103791-35-1 MDL No.:MFCD09035272 MF:C10H13NO MW:163.2163 |
Thiomorpholine-3-carboxamideCatalog No.:AA009SIN CAS No.:103742-31-0 MDL No.:MFCD02666349 MF:C5H10N2OS MW:146.2107 |
4-((2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)-N-(prop-2-yn-1-yl)cyclohexanecarboxamideCatalog No.:AA00HA2Y CAS No.:1036847-90-1 MDL No.:MFCD27956997 MF:C15H18N2O3 MW:274.3150 |
4-[(1-Azetidinyl)methyl]phenylboronic acid pinacol esterCatalog No.:AA00HA31 CAS No.:1036990-23-4 MDL No.:MFCD18735839 MF:C16H24BNO2 MW:273.1783 |
5-[(Hexahydro-1H-1,4-diazepin-1-yl)sulfonyl]isoquinolineCatalog No.:AA00HA3M CAS No.:103745-39-7 MDL No.:MFCD00153805 MF:C14H17N3O2S MW:291.3687 |
Methyl 5,8-dioxaspiro[3.4]octane-2-carboxylateCatalog No.:AA00HA3E CAS No.:1037175-81-7 MDL No.:MFCD23106444 MF:C8H12O4 MW:172.1785 |
N,3-Dimethylpyridine-2-carboxamideCatalog No.:AA00HA37 CAS No.:1037045-67-2 MDL No.:MFCD19671808 MF:C8H10N2O MW:150.1778 |
6-(4-Fluorophenyl)pyrazolo[1,5-a]pyrimidineCatalog No.:AA00HA2W CAS No.:1036762-04-5 MDL No.:MFCD28405285 MF:C12H8FN3 MW:213.2104 |
4-Tert-butyl-2,6-dichloropyrimidineCatalog No.:AA00HA3O CAS No.:1037535-38-8 MDL No.:MFCD18916413 MF:C8H10Cl2N2 MW:205.0844 |
1,3,2-Dioxaborolane, 2-(3-methoxy-5-nitrophenyl)-4,4,5,5-tetramethyl-Catalog No.:AA00HA30 CAS No.:1036990-22-3 MDL No.:MFCD22493664 MF:C13H18BNO5 MW:279.0967 |
1-ethyl-4-[3-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]piperazineCatalog No.:AA00HA33 CAS No.:1036990-36-9 MDL No.:MFCD22415367 MF:C19H29BN2O3 MW:344.2562 |
N-(3-bromophenyl)oxan-4-amineCatalog No.:AA00ILLZ CAS No.:1036990-31-4 MDL No.:MFCD12087567 MF:C11H14BrNO MW:256.1390 |
1,5-Dimethyl-4-phenylimidazolidin-2-oneCatalog No.:AA00IOHM CAS No.:103774-40-9 MDL No.:MFCD01456559 MF:C11H14N2O MW:190.2417 |
3-(dimethylamino)-2-(2,2,2-trifluoroacetyl)acrylonitrileCatalog No.:AA00IQD3 CAS No.:1037593-80-8 MDL No.:MFCD00664325 MF:C7H7F3N2O MW:192.1385 |
8-Methyl-1-thia-4-azaspiro[4.5]decane-3-carboxylic acidCatalog No.:AA00IW7B CAS No.:1037010-80-2 MDL No.:MFCD06633105 MF:C10H17NO2S MW:215.3125 |
2-[(Z)-(2,4-dichlorophenyl)methylidene]-3-quinuclidinolCatalog No.:AA00IYYV CAS No.:1037240-01-9 MDL No.:MFCD05256359 MF:C14H15Cl2NO MW:284.1810 |
methyl 5-amino-1-benzyl-1H-1,2,3-triazole-4-carboxylateCatalog No.:AA00J0IO CAS No.:103742-39-8 MDL No.:MFCD00100211 MF:C11H12N4O2 MW:232.2386 |
4,4-dimethyl-1-piperidinesulfonyl chlorideCatalog No.:AA00J2AT CAS No.:1037041-50-1 MDL No.:MFCD17253007 MF:C7H14ClNO2S MW:211.7096 |
2-hydrazino-5,6-dihydrobenzo[h]quinazolineCatalog No.:AA00J2KP CAS No.:1037784-17-0 MDL No.:MFCD22575213 MF:C12H12N4 MW:212.2505 |
3-bromo-1,2,4-thiadiazoleCatalog No.:AA00J3BU CAS No.:1036990-54-1 MDL No.:MFCD11848380 MF:C2HBrN2S MW:165.0117 |
2-(4-ethoxyphenyl)acetyl chlorideCatalog No.:AA00J6U2 CAS No.:10368-35-1 MDL No.:MFCD00995155 MF:C10H11ClO2 MW:198.6461 |
Ethyl N-(6-methylpyridin-2-yl)carbamateCatalog No.:AA00L6QE CAS No.:103796-10-7 MDL No.:MFCD00956975 MF:C9H12N2O2 MW:180.2038 |
2-methoxy-N-[4-(tetramethyl-1，3，2-dioxaborolan-2-yl)phenyl]acetamideCatalog No.:AA00QGGB CAS No.:1036990-20-1 MDL No.:MFCD22494280 MF:C15H22BNO4 MW:291.1505 |
4-Isopropyloxazolidin-2-oneCatalog No.:AA018RZ2 CAS No.:103723-70-2 MDL No.:MFCD11041014 MF:C6H11NO2 MW:129.1570 |
[1-(3-fluorophenyl)cyclobutyl]methanamineCatalog No.:AA019CYM CAS No.:1037131-77-3 MDL No.:MFCD11188946 MF:C11H14FN MW:179.2340 |
4-Ethoxybutanoic acidCatalog No.:AA019NBD CAS No.:10374-37-5 MDL No.:MFCD09928843 MF:C6H12O3 MW:132.1577 |
[2-chloro-6-(4-methylpiperazin-1-yl)phenyl]methanamineCatalog No.:AA019SL1 CAS No.:1037161-38-8 MDL No.:MFCD11191625 MF:C12H18ClN3 MW:239.7444 |
methyl 4-(2,6-difluorophenyl)-2,4-dioxobutanoateCatalog No.:AA019U9F CAS No.:1037130-74-7 MDL No.:MFCD11188865 MF:C11H8F2O4 MW:242.1756 |
3-[(5-methylpyridin-2-yl)amino]propanoic acidCatalog No.:AA019UUQ CAS No.:103796-00-5 MDL No.:MFCD09877624 MF:C9H12N2O2 MW:180.2038 |
[4-(2,6-dimethylmorpholin-4-yl)-3-fluorophenyl]methanamineCatalog No.:AA019VDY CAS No.:1037161-46-8 MDL No.:MFCD11191630 MF:C13H19FN2O MW:238.3012 |
4-Amino-N-(3-chloro-4-fluorophenyl)benzenesulfonamideCatalog No.:AA019VSK CAS No.:1037132-84-5 MDL No.:MFCD12559329 MF:C12H10ClFN2O2S MW:300.7364 |
[3-Fluoro-4-(2-methyl-1H-imidazol-1-yl)phenyl]methanamineCatalog No.:AA019XDR CAS No.:1037163-76-0 MDL No.:MFCD11191729 MF:C11H12FN3 MW:205.2315 |
3-(2,5-dimethoxyphenyl)-1H-pyrazole-5-carbohydrazideCatalog No.:AA01A0PZ CAS No.:1037690-39-3 MDL No.:MFCD02668327 MF:C12H14N4O3 MW:262.2646 |
2-Bromo-5-chlorobenzene-1-sulfonyl chlorideCatalog No.:AA01A1FA CAS No.:1037299-72-1 MDL No.:MFCD18379727 MF:C6H3BrCl2O2S MW:289.9618 |
3-cyclohexyl-1H-pyrazole-5-carboxylic acidCatalog No.:AA01A2VE CAS No.:1037061-95-2 MDL No.:MFCD17193820 MF:C10H14N2O2 MW:194.2304 |
2-(tert-butoxy)pyridine-4-carbonitrileCatalog No.:AA01A3R6 CAS No.:1037131-17-1 MDL No.:MFCD11196883 MF:C10H12N2O MW:176.2151 |
2-chloro-1-{1H-pyrrolo[2,3-b]pyridin-3-yl}propan-1-oneCatalog No.:AA01A3RD CAS No.:1037152-84-3 MDL No.:MFCD11189414 MF:C10H9ClN2O MW:208.6443 |
(thiomorpholin-3-yl)methanamineCatalog No.:AA01A452 CAS No.:103742-33-2 MDL No.:MFCD19207011 MF:C5H12N2S MW:132.2272 |
2-Methyl-1,2,3,4-tetrahydronaphthalen-1-amineCatalog No.:AA01A4ZG CAS No.:103791-10-2 MDL No.:MFCD09035035 MF:C11H15N MW:161.2435 |
3-([(3-Methylcyclohexyl)oxy]methyl)anilineCatalog No.:AA01A7K8 CAS No.:1037157-93-9 MDL No.:MFCD11196406 MF:C14H21NO MW:219.3226 |
4-[benzyl(ethyl)amino]benzoic acidCatalog No.:AA01A8CB CAS No.:1037132-10-7 MDL No.:MFCD11923146 MF:C16H17NO2 MW:255.3117 |
[1-(2-methylphenyl)cyclohexyl]methanamineCatalog No.:AA01A8Q6 CAS No.:1037131-52-4 MDL No.:MFCD11188923 MF:C14H21N MW:203.3232 |
(4-Ethoxy-3-fluorophenyl)methanamineCatalog No.:AA01AB21 CAS No.:1037164-60-5 MDL No.:MFCD11191786 MF:C9H12FNO MW:169.1961 |
4-Chloro-1-methyl-1H-1,3-benzodiazol-2-amineCatalog No.:AA01AC7H CAS No.:1037670-19-1 MDL No.:MFCD20724208 MF:C8H8ClN3 MW:181.6222 |
3-(2,6-Dichlorophenyl)-2-methylprop-2-enoic acidCatalog No.:AA01ACBL CAS No.:103753-79-3 MDL No.:MFCD00666051 MF:C10H8Cl2O2 MW:231.0753 |
1-[4-(2-methylpropoxy)phenyl]cyclobutane-1-carboxylic acidCatalog No.:AA01AH1H CAS No.:1037131-39-7 MDL No.:MFCD11541476 MF:C15H20O3 MW:248.3175 |
1-(cyclopropanesulfonyl)piperidine-4-carboxylic acidCatalog No.:AA01AQHH CAS No.:1036738-97-2 MDL No.:MFCD16653434 MF:C9H15NO4S MW:233.2847 |
2-(Benzylsulfanyl)ethanimidamide hydrochlorideCatalog No.:AA01B18Y CAS No.:10378-68-4 MDL No.:MFCD28012189 MF:C9H13ClN2S MW:216.7309 |
4-(2-Fluorophenyl)-1h-pyrazoleCatalog No.:AA01B1L6 CAS No.:1037828-70-8 MDL No.:MFCD19313355 MF:C9H7FN2 MW:162.1637 |
Methyl (2S)-1-(prop-2-yn-1-yl)pyrrolidine-2-carboxylateCatalog No.:AA01B2HJ CAS No.:103711-16-6 MDL No.:MFCD29991645 MF:C9H13NO2 MW:167.2050 |
2-(diethylamino)ethyl 3-aminobenzoateCatalog No.:AA01B9QS CAS No.:10369-94-5 MDL No.:MFCD13425220 MF:C13H20N2O2 MW:236.3101 |
2-Chloro-1-(4,4-difluorocyclohexyl)ethan-1-oneCatalog No.:AA01BE52 CAS No.:1037834-16-4 MDL No.:MFCD18375008 MF:C8H11ClF2O MW:196.6221 |
1-(4-Bromo-2-methylphenyl)-N-methylmethanamineCatalog No.:AA01BEBB CAS No.:1037090-12-2 MDL No.:MFCD12096719 MF:C9H12BrN MW:214.1023 |
(2S)-2-[(4-chlorophenyl)amino]propanoic acidCatalog No.:AA01BGN4 CAS No.:103678-25-7 MDL No.:MFCD20641844 MF:C9H10ClNO2 MW:199.6342 |
2-[(2-methylbutan-2-yl)oxy]ethan-1-amineCatalog No.:AA01C22Y CAS No.:1037131-98-8 MDL No.:MFCD11196454 MF:C7H17NO MW:131.216 |
1-(2,4-dichlorophenyl)cyclohexane-1-carbonitrileCatalog No.:AA01C24S CAS No.:1037130-92-9 MDL No.:MFCD11036796 MF:C13H13Cl2N MW:254.155 |
4-[(tert-butoxy)carbonyl]oxane-4-carboxylic acidCatalog No.:AA01C25E CAS No.:1036922-77-6 MDL No.:MFCD30342619 MF:C11H18O5 MW:230.2576 |
3-O-Acetyl-betulinic acidCatalog No.:AA01CBBS CAS No.:10376-50-8 MDL No.:MFCD04972177 MF:C32H50O4 MW:498.7370 |
2-(4-methanesulfonamidophenoxy)acetic acidCatalog No.:AA01CCG3 CAS No.:103790-20-1 MDL No.:MFCD14529530 MF:C9H11NO5S MW:245.2523 |
(3S)-2-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidCatalog No.:AA01DQ6Y CAS No.:103775-10-6 MDL No.:MFCD00865878 MF:C27H34N2O7 MW:498.5681 |
6-ethylpiperidine-2-carboxylic acidCatalog No.:AA01DUUX CAS No.:1037471-93-4 MDL No.:MFCD26045085 MF:C8H15NO2 MW:157.2102 |
2-Chloro-N,N-dimethyl-5-nitrobenzenesulfonamideCatalog No.:AA01DX4U CAS No.:10372-90-4 MDL No.:MFCD09699506 MF:C8H9ClN2O4S MW:264.6861 |
6-tert-Butylpyridine-3-sulfonyl chlorideCatalog No.:AA01DX4V CAS No.:1037241-40-9 MDL No.:MFCD19201254 MF:C9H12ClNO2S MW:233.7151 |
1-(2-chloro-6-fluorophenyl)cyclobutane-1-carboxylic acidCatalog No.:AA01DX4S CAS No.:1037131-07-9 MDL No.:MFCD11037026 MF:C11H10ClFO2 MW:228.6473 |
6-(propan-2-yloxy)-1,2,3,4-tetrahydroquinolineCatalog No.:AA01DX4T CAS No.:1037163-65-7 MDL No.:MFCD11192493 MF:C12H17NO MW:191.2695 |
O-β-D-Glucopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→3)-O-β-D-glucopyranosyl-(1→4)-D-glucoseCatalog No.:AA01EAY0 CAS No.:103762-93-2 MDL No.:MFCD28064311 MF:C24H42O21 MW:666.5777 |
3-Amino-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrileCatalog No.:AA01EHL3 CAS No.:1036991-35-1 MDL No.:MFCD22494384 MF:C13H17BN2O2 MW:244.0973 |
N-(2-Aminoethyl)-2-(4-fluorophenyl)acetamide hydrochlorideCatalog No.:AA01EJ73 CAS No.:1037411-95-2 MDL No.:MFCD31666326 MF:C10H14ClFN2O MW:232.6824 |
1-Bromo-3,5-dimethoxy-4-iodobenzeneCatalog No.:AA01ELD9 CAS No.:1037082-67-9 MDL No.:MFCD28738448 MF:C8H8BrIO2 MW:342.9564 |
Carbamic acid,N-[2-[[[[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amino]carbonyl]amino]ethyl]-, 1,1-dimethylethyl esterCatalog No.:AA01FNQ4 CAS No.:1036990-28-9 MDL No.:MFCD32206586 MF:C20H32BN3O5 MW:405.2962 |
2-Amino-4-bromo-5-chlorophenolCatalog No.:AA0096XF CAS No.:1037298-14-8 MDL No.:MFCD25978069 MF:C6H5BrClNO MW:222.4670 |
Potassium perruthenateCatalog No.:AA003TUB CAS No.:10378-50-4 MDL No.:MFCD00061333 MF:KO4Ru MW:204.1659 |
Manganese nitrateCatalog No.:AA0085C8 CAS No.:10377-66-9 MDL No.:MFCD00149788 MF:MnN2O6 MW:178.9478 |
2,6-Dichloro-N-(2,6-dimethylphenyl)hexanamideCatalog No.:AA008VNM CAS No.:1037184-07-8 MDL No.:MFCD25371999 MF:C14H19Cl2NO MW:288.2128 |
(5aS,6R,9S,9aR)-5a,6,7,8,9,9a-Hexahydro-6,11,11-trimethyl-2-(2,3,4,5,6-pentafluorophenyl)-6,9-methano-4H-[1,2,4]triazolo[3,4-c][1,4]benzoxazinium tetrafluoroborateCatalog No.:AA008WE5 CAS No.:1037287-81-2 MDL No.:MFCD28144540 MF:C19H19BF9N3O MW:487.1703 |
(5aS,6R,9S,9aR)-2-Mesityl-6,11,11-trimethyl-5a,6,7,8,9,9a-hexahydro-4H-6,9-methanobenzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborateCatalog No.:AA008X0V CAS No.:1037287-79-8 MDL No.:MFCD28144541 MF:C22H30BF4N3O MW:439.2977 |
6-Iodo-7-methyl-imidazo[1,2-a]pyridineCatalog No.:AA0093HW CAS No.:1036991-04-4 MDL No.:MFCD23115412 MF:C8H7IN2 MW:258.0591 |
(2-Amino-5-bromo-4-chlorophenyl)methanolCatalog No.:AA0093IX CAS No.:1036757-10-4 MDL No.:MFCD20037891 MF:C7H7BrClNO MW:236.4936 |
2-Amino-5-bromo-4-chlorobenzaldehydeCatalog No.:AA0096US CAS No.:1036757-11-5 MDL No.:MFCD20037890 MF:C7H5BrClNO MW:234.4777 |
6-fluoro-5-methyl-1H-indazol-3-amineCatalog No.:AA0096V1 CAS No.:1037206-99-7 MDL No.:MFCD16658719 MF:C8H8FN3 MW:165.1676 |
(6-Amino-3-bromo-2-fluorophenyl)methanolCatalog No.:AA01FR30 CAS No.:1036756-04-3 MDL No.:MFCD30723666 MF:C7H7BrFNO MW:220.0390 |
6-Amino-3-bromo-2-fluorobenzaldehydeCatalog No.:AA01FR4F CAS No.:1036756-05-4 MDL No.:MFCD30471489 MF:C7H5BrFNO MW:218.0231 |
3-amino-1-[4-(propan-2-yloxy)phenyl]thioureaCatalog No.:AA01A9QA CAS No.:1037165-03-9 MDL No.:MFCD11192533 MF:C10H15N3OS MW:225.3106 |
(3aR,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetateCatalog No.:AA01DK1B CAS No.:10378-06-0 MDL No.:MFCD28992015 MF:C14H19NO8 MW:329.3026 |