Day: March 25, 2022

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1059630-08-8,(4aS,9bR)-Ethyl 6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate,as a common compound, the synthetic route is as follows.

Example 4: Production of [4aS,9bR] -ethyl 5-(2-amino-2-oxoethyl)-6-bromo- 3,4,4a,5-tetrahydro-lH-pyrido[4,3-b]indole-2(9bH)-carboxylate; (4aS,9bR)-ethyl 5-(2-amino-2-oxoethyl)-6-bromo-3,4,4a,5-tetrahydro- lH-pyrido[4,3-b]indole-2(9bH)-carboxylate may be prepared by heating to a reflux a suspension of (4aS,9bR)-ethyl 6-bromo-3,4,4a,5-tetrahydro- 1 H-pyrido[4,3-b]indole- 2(9bH)-carboxylate (5.648g, 17.4mmol), 2-chloroacetamide (7.32g, 78.2mmol), potassium iodide (19.2g, 77.7mol) and diisopropylethylamine (19mL, 115mmol) in acetonitrile (8OmL) for 27 hours. The solvent is removed in a vacuo and water (20OmL) is added to the residue and stirred for 1 hour. The resulting white solid is filtered off, washed with ethanol and dried., 1059630-08-8

1059630-08-8 (4aS,9bR)-Ethyl 6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate 59317960, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; INTRA-CELLULAR THERAPIES, INC.; WO2008/112280; (2008); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1186663-64-8,3-Bromo-1H-indole-4-carbonitrile,as a common compound, the synthetic route is as follows.

3-Bromo?l H-mdole-4-carboimrile (l-146a: 5OU mg, 2.272 mmol) was added dropwise. tupsilon a stirred mixture of NaI 1 (0.218 g, 9.0833 mmol) in dry DMl- ( 15 ml ) at OT over a period of 10 minutes. This was followed b>- the addition of methyl iodide and the resulting mixture was stirred at O0C for -? hours. The reaction was monitored by Tl, C (10% cth) lacctatc in hcxane). The reaction mixture was quenched with ice water: the precipitate formed was collected and dried to afford 0.400 g of the crude product.1H NMR (CDCl,, 300 MH/): delta 7.8-7.0 (m, 411), 3.82 (s, 3H)

1186663-64-8, The synthetic route of 1186663-64-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; NOVARTIS AG; BOCK, Mark G.; GAUL, Christoph; GUMMADI, Venkateshwar Rao; SENGUPTA, Saumitra; WO2010/149755; (2010); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

938465-52-2, 1-Chloro-5H-pyrido[4,3-b]indole-4-carboxamide is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,938465-52-2

A mixture of l-chloro-5H-pyrido[4,3-6]indole-4-carboxamide in cone. NH4OH (0.07 M) was heated in a microwave reactor at 1600C for 1 h in a sealed tube. The reaction mixture was cooled to room temperature and partitioned between THF/EtOAc and saturated NaHCO3. After separation of the organic phase, the aqueous phase was extracted again with THF/EtOAc, and the combined organic phases were washed with brine, dried over Na2SCXj and filtered. After evaporation of the organic solvents, the residue was purified by flash chromatography (0-10% MeOH in EtOAc) to provide the title compound as an off-white solid.1H NMR (DMSO-d6) delta 11.50 (IH, s), 8.50 (IH, s), 8.30 (IH, d), 7.85 (IH, br s), 7.75 (IH, d), 7.35 (IH, t), 7.20 (IH, t), 7.15 (IH, br s), 6.80 (2H, br s).

The synthetic route of 938465-52-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; MERCK & CO., INC.; MERCK FROSST CANADA LTD.; WO2007/61764; (2007); A2;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

72016-68-3,72016-68-3, Ethyl 2-(5-bromo-2-methyl-1H-indol-3-yl)acetate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2 Ethyl 2-(5-bromo-1-(4-iodobenzyl)-2-methyl-1H-indol-3-yl)acetate To a solution of the product of Step 1 (536.2 mg, 2 mmol) and 4-iodobenzyl chloride (504 mg, 2 mmol) in dry DMF (10 mL) at 0 C. was added sodium hydride (80 mg, 2 mmol, 60% in oil). The mixture was stirred at 20 C. for 20 hours and a saturated NH4 Cl solution (10 mL) was added. The mixture was extracted with EtOAc, the extracts were dried over MgSO4 and concentrated to an oil. The oil was purified by flash chromatography on silica gel, eluding with 20% EtOAc in hexane to afford 704 mg (69%) of the title compound. 1 H NMR (CDCl3) 1.23 (3H, t, J=7.1 Hz), 2.28 (3H, s), 3.65 (2H, s), 4.12 (2H, q, J=7.1 Hz), 5.19 (2H, s), 6.64 (2H, d, J=8.3 Hz), 6.98 (1H, d, J=8.6 Hz), 7.17 (1H, dd, J=8.6 Hz, 1.8 Hz), 7.56 (2H, d, J=8.3 Hz), 7.68 (1H, d, 1.8 Hz).

The synthetic route of 72016-68-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Merck Frosst Canada, Inc.; US5510368; (1996); A;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.53924-05-3,7-Chloroindole,as a common compound, the synthetic route is as follows.,53924-05-3

General procedure: POCl3 (13.09 g, 85.36 mmol) was slowly added dropwise to DMF(10 mL) under ice bath. The mixture was stirred at ice bath for30 min. Then, DMF (6.24 g, 85.36 mmol) solution of indole (5 g,42.68 mmol) was added dropwise to the reaction system. Keepingthe reaction at room temperature for 3 h, ice water and 10% NaOHaq. were added into the reaction system to pH of 7-8 and continue to stir to a lot of white solid precipitation. The solid was recrystallizedfrom ethyl acetate and petroleum ether to obtain compound3 in yields of 97.6%.

53924-05-3 7-Chloroindole 104644, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Liu, Hong-Min; Suo, Feng-Zhi; Li, Xiao-Bo; You, Ying-Hua; Lv, Chun-Tao; Zheng, Chen-Xing; Zhang, Guo-Chen; Liu, Yue-Jiao; Kang, Wen-Ting; Zheng, Yi-Chao; Xu, Hai-Wei; European Journal of Medicinal Chemistry; vol. 175; (2019); p. 357 – 372;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.162100-95-0,6-Fluoro-5-methyl-1H-indole,as a common compound, the synthetic route is as follows.

Diethylaluminum chloride 1M in hexane (25.1 mL, 25.1 mmol) was addeddropwise, at 000 and under N2-flow, to a solution of 6-fluoro-5-methyl-1 H-indole[CAS 162100-95-0] (2.5 g, 16.8 mmol) in CH2CI2 (135 mL). After 10 mm at 0C, a solution of 2-(2-(2-(benzyloxy)ethoxy)-4-fluorophenyl)acetyl chloride le (8.11 g, 25.1 mmol) in CH2CI2 (50 mL) was added dropwise at 0C over a period of 45 mm, while keeping the reaction temperature below 5C. The reaction was stirred at 0Cfor 2 h and at 10C for 2 h. The reaction mixture was cooled to 0C, and a solution of Rochelle salt [6100-16-9] (9.46 g, 33.5 mmol) in water (10 mL) was added dropwise. After addition, the reaction mixture was stirred at 0C for 10 minutes and then allowed to warm to room temperature. THE (150 mL) and Na2SO4 (40 g) were added, and the mixture was stirred for 18 h. The mixture was filtered overdicalite and washed with plenty of THE. The combined filtrates were evaporated under reduced pressure, and co-evaporated with toluene. The residue was crystallized from CH3CN (10 mL), filtered off, washed with CH3CN (2x), and dried under vacuum at 40C to provide a first fraction of 2-(2-(2-(benzyloxy)ethoxy)- 4-fluorophenyl)-1 -(6-fluoro-5-methyl-1 H-indol-3-yl)ethanone 7a (1 .86 g). Thefiltrate was evaporated under reduced pressure. The residue (7.7 g) was purified by flash chromatography (Stationary phase: Grace Reveleris silica 120 g, Mobile phase: heptane/EtOAc gradient 100/0 to 0/1 00). The fractions containing product were combined and left standing in an open recipient to allow evaporation of the solvent and crystallization of the product. The precipitate was isolated by filtration,washed 3x with heptane/EtOAc (1/1) and dried under vacuum at 40C to provide a second (1 .51 g) and third (0.75 g) fraction of intermediate 7a., 162100-95-0

162100-95-0 6-Fluoro-5-methyl-1H-indole 2774611, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; KESTELEYN, Bart Rudolf Romanie; RABOISSON, Pierre Jean-Marie Bernard; BONFANTI, Jean-Francois; JONCKERS, Tim Hugo Maria; BARDIOT, Dorothee Alice Marie-Eve; MARCHAND, Arnaud Didier M; (70 pag.)WO2017/46258; (2017); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

101495-18-5, 4,6-Dichloro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step b Ethyl 2,-(hydroxyimino)-3-(4,6-dichloro-3-indolyl)propanoate Mix 4,6-dichloroindole (5.90g, 31.72mmol), potassium carbonate (1.81g, 47.6mmol) and anhydrous methylene chloride (200mL). Stir and add a solution of ethyl 3-bromo-2-hydroxyiminopropanoate (7.00g, 33.31mmol) in methylene chloride (75mL). Stir under a nitrogen atmosphere for 48 hours. Take the solution up in methylene chloride (100mL) and wash with water (300mL), saturated sodium hydrogen carbonate (200mL) and brine (100mL). Dry (MgSO4) and evaporate the solvent in vacuo to give a tan solid. Purify by silica gel chromatography (1 to 3% acetone in chloroform) to give the title compound as a yellow solid (7.00g, 99% based on consumed starting material). Recrystallize (diethyl ether/hexane) to give the tit le compound as white crystals (4.0g, 56%); mp 175-176 C. 1 H NMR (DMSO-d6 /TMS): 1.19 ppm (3H, t), 4.15 ppm (2H, q), 4.15 ppm (2H, s), 6.95 ppm (1H, s), 7.10 ppm (1H, d), 7.40 ppm (1H, d), 11.3 ppm (1H, bs), 12.35 (1H, s)., 101495-18-5

The synthetic route of 101495-18-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Merrell Dow Pharmaceuticals Inc.; US5360814; (1994); A;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

1145678-74-5, (1-Tosyl-1H-indol-4-yl)methanamine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 31-((1H-indol-4-yl)methyl)-9-(4,6-dimethylpyrimidin-2-yl)-1,9-diazaspiro[5.5]undecan-2-one a) tert-butyl 4-allyl-4-((1-tosyl-1H-indol-4-yl)methylamino)piperidine-1-carboxylate; To a stirred mixture of 1-Boc-piperidin-4-one (0.25 g, 1.256 mmol), 4 molecular sieves (0.25 g), allyl boronic acid pinacol ester (0.255 g, 1.507 mmol) in toluene (10.0 mL), 1-tosyl-1H-indol-4-yl)methanamine (0.45 g, 1.507 mmol) was added and the reaction mixture was heated to reflux for 16 h. The mixture was filtered through a pad of celite. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (eluent: 10% ethyl acetate in hexane) to yield the title compound as a white solid (0.2 g, 70%). [LCMS RtE=0.341, [M+H]+=524.0]

1145678-74-5, 1145678-74-5 (1-Tosyl-1H-indol-4-yl)methanamine 67262154, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; BADIGER, Sangamesh; BEHNKE, Dirk; BETSCHART, Claudia; COTESTA, Simona; HINTERMANN, Samuel; OFNER, Silvio; PANDIT, Chetan; ROY, Bernard Lucien; US2012/101110; (2012); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.312314-26-4,4-(Benzyloxy)-6-fluoro-1H-indole,as a common compound, the synthetic route is as follows.

To a solution of compound l-5b (559 mg, 2.32 mmol) in 70 mL ether, oxalyl chloride was added slowly at O C. After 10 min, the reaction mixture was warmed to room temperature and stirred for 6 h. After the mixture was cooled to O C, Et3N (3.0 mL) and MeOH (3.0 mL) were introduced and the resulting mixture was stirred overnight. The reaction mixture was diluted with water and extracted with EtOAc 2 X 100 mL, the combined organic phase was washed by brine and dried over Na2SO4. After concentration, the crude product 26-1 was obtained as a brown oil (897 mg), which was used in the next step without purification. 1H NMR (CDCl3, 300 MHz) delta (ppm): 9.09 (bs, 1H), 8.00 (d, J=3.0Hz, 1H), 7.50 (d, J=7.1Hz, 2H), 7.28-7.41 (m, 3H), 6.72 (dd, J=1.9, 8.3Hz, 1H), 6.51 (dd, J=1.9, 11.7Hz, 1H), 5.20 (s, 2H), 3.67 (s, 3H)., 312314-26-4

312314-26-4 4-(Benzyloxy)-6-fluoro-1H-indole 10610125, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; GALENEA CORPORATION; ELDER, Amy; HARRIMAN, Geraldine; LEIT, Silvana; LI, Jie; SARD, Howard; ZHANG, Yiliang; WILSON, Doug; WO2011/19738; (2011); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

434958-85-7, N-Boc-5-Hydroxyindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1-(tert-Butoxycarbonyl)-5-hydroxyindole (2.33 g, 10.0 mmol) and triphenylphosphine (5.25 g, 20.0 mmol) were dissolved in toluene (46.0 mL), and the solution was added with glycidol (1.32 mL, 20.0 mmol) and 40% DEAD-toluene solution (9.10 mL, 20 mmol) at room temperature, followed by stirring at 80C for 4 hours. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography (hexane/ethyl acetate=4/1). A crude product (1.28 g) of 1-(tert-butoxycarbonyl)-5-hydroxyindole (1.28 g) was obtained. The obtained crude product was dissolved in N,N-dimethylacetoamide (20.0 mL), and the solution was added with 2- (ethylamino) ethanol (8.60 mL, 87.8 mmol), followed by stirring at 80C for 4 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography (chloroform/methanol =9/1) to obtain 1-(tert-butoxycarbonyl)-5-{3-[N-ethyl(2-hydroxyethyl)amino]-2-hy droxypropoxy}indole (1.53 g, 40%). ESI-MS m/z: 379 [M+H]+; 1H-NMR (CDCl3)delta(ppm): 1.07 (t, J = 7.2 Hz, 3H), 1.66 (s, 9H), 2.61-2.80 (m, 6H), 3.61-3.68 (m, 2H), 3.99-4.14 (m, 3H), 6.48 (d, J = 3.9 Hz, 1H), 6.94 (dd, J = 2.6, 8.7 Hz, 1H), 7.04 (d, J = 2.6 Hz, 1H), 7.56 (d, J = 3.9 Hz, 1H), 8.01 (d, J = 8.7 Hz, 1H).

434958-85-7, The synthetic route of 434958-85-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2108642; (2009); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles