Day: March 25, 2022

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.399-51-9,6-Fluoro-1H-indole,as a common compound, the synthetic route is as follows.

General procedure: A 50 mL round-bottomed flask equipped with a magnetic stirringbar was charged with the appropriate indole 1 (0.5 mmol,1.0 equiv), 37% aq HCHO (0.5 mmol, 0.0406 g, 1.0 equiv), 25% aqNH3 (1.0 mmol, 0.0681 g, 2.0 equiv), FeCl3 (0.01 mmol, 0.0016 g,2 mol%), and DMF (2 mL). The flask was fitted with a reflux condenser,and the mixture was stirred at 130 C under open air.When the reaction was complete (TLC), the mixture was cooledto r.t., diluted with sat. aq NaCl (10 mL) and 0.5 M aq HCl (2 mL),and extracted with EtOAc (3 x 7 mL). The organic layers werecombined, washed with sat. aq NaHCO3 (10 mL) and sat. aq NaCl(10 mL), dried (Na2SO4), and concentrated under reduced pressure.The residue was purified by flash column chromatography(silica gel, hexane-EtOAc).

399-51-9, As the paragraph descriping shows that 399-51-9 is playing an increasingly important role.

Reference：
Article; Wang, Qing-Dong; Zhou, Bin; Yang, Jin-Ming; Fang, Dong; Ren, Jiangmeng; Zeng, Bu-Bing; Synlett; vol. 28; 19; (2017); p. 2670 – 2674;,
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.289483-82-5,4-Methyl-7-nitro-1H-indole-3-carbonitrile,as a common compound, the synthetic route is as follows.

289483-82-5, Example 2A; Synthesis of 7-amino-3-cyano-4-methyl-1H-indole; After suspending 400 g (1.99 mol) of the 3-cyano-4-methyl-7-nitro-1H-indole obtained in Example 1A in a mixture of 6 L of ethyl acetate and 6 L of methanol, the suspension was subjected to hydrogenation in the presence of 40 g of 10% palladium-carbon at ordinary temperature, 4 atmospheres. After removing the catalyst by filtration, the filtrate was treated with activated carbon and concentrated to give crude crystals. The crude crystals were dissolved in 6 L of 1,2-dimethoxyethane at an external temperature of 60 C., and then 12 L of water was added dropwise. Upon confirming precipitation of crystals, the mixture was stirred for 1.5 hours while cooling in an ice bath and filtered, and the crystals were washed twice with water (1 L). The crystals were air-dried at 50 C. for 16 hours to give 289 g of the title compound (yield: 84.8%). HPLC analysis confirmed that the obtained compound was identical to the 7-amino-3-cyano-4-methyl-1H-indole described in WO00/50395. (HPLC conditions) Mobile phase: CH3CN/H2O/70% HClO4=400/600/1 (v/v/v) Flow rate: 1.0 mL/min Detection: UV (282 nm) Column: YMC-Pack Pro C18 250×4.6 mm

The synthetic route of 289483-82-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Hayashi, Kenji; Abe, Taichi; Ozeki, Naoki; Akamatsu, Hiroshi; US2007/37854; (2007); 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 4-((benzyloxy)methyl)-2-methyl-2,7-diazaspiro[4. s1 decan- 1-one(118 mg, 0.407 mmol), 1-chloro-5H-pyrido[4,3-bjindole-4-carboxamide (100 mg, 0.407 mmol)and DIPEA (0.3 mL, 1.63 mmol) in 1-methylpyrrolidin-2-one (3 mL) was stirred in a microwave at 150 C for 2 h. To the mixture was added water (10 mL). The mixture was extracted withDCM/i-PrOH (3:1, 20 mL )< 3). The combined organic layers were washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated to afford the crude product, which waspurified by silica gel column chromatography (THF / PE = 30% 80 %) to give 1-(4-((benzyloxy)methyl)-2-methyl- 1 -oxo-2,7-diazaspiro [4.51 decan-7-yl)-5H-pyrido [4,3-bj indole-4-+carboxamide as a solid. MS: 498.2[M+Hj As the paragraph descriping shows that 938465-52-2 is playing an increasingly important role. Reference：
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph; KIM, Ronald; GAO, Xiaolei; BOGA, Sobhana Babu; YU, Younong; WU, Hao; LIU, Shilan; YANG, Chundao; (102 pag.)WO2016/164284; (2016); 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.289483-82-5,4-Methyl-7-nitro-1H-indole-3-carbonitrile,as a common compound, the synthetic route is as follows.

Production Example 12 7-Amino-3-cyano-4-methyl-1H-indole 12.6 g (62.6 mmol) of the compound of Production Example 6 was dissolved in a mixed solution of 100 ml of tetrahydrofuran and 100 ml of methanol, and the mixture was hydrogenated at an ordinary temperature under 3 atoms in the presence of 430 mg (1.87 mmol) of platinum oxide. The catalyst was filtered off and the filtrate was concentrated to dryness. Then, a mixed solution of tert-butyl methyl ether and hexane was added to the residue and the crystals were collected by filtration, to give 10.7 g of the title compound. 50.5 g (186 mmol) of the compound of Production Example 11 was dissolved in 400 ml of dichloromethane. In nitrogen atmosphere, 210 ml (2.76 mol) of trifluoroacetic acid was added thereto at 0C, followed by stirring at room temperature for 40 minutes. The reaction mixture was adjusted to pH 7 by adding a 5N aqueous sodium hydroxide thereto. The solvent was removed, and then the residue was extracted with ethyl acetate. The organic layer was successively washed with water and brine, dried over magnesium sulfate and concentrated to dryness. A mixed solution of diethyl ether and hexane was added to the residueand the crystals were collected by filtration, to give 24.5 g of the title compound. 1H-NMR(DMSO-d6) delta (ppm): 2.47(3H, s), 5.07 (2H, s), 6.34(1H, d, J=7.6Hz), 6.64(1H, d, J=7.6Hz), 8.10(1H, s), 11.70(1H, br s)

289483-82-5, 289483-82-5 4-Methyl-7-nitro-1H-indole-3-carbonitrile 11622527, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Eisai Co., Ltd.; EP1258252; (2002); 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

923197-75-5, (6-Bromo-1H-indol-2-yl)methanol is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,923197-75-5

(6-Bromo-1H-indol-2-yl)methanol (80 mg, 0.35 mmol) and dess-martin periodinane (178 mg, 0.42 mmol) were dissolved in dichloromethane (10 mL), and it was stirred for 30 minutes at room temperature. The reaction mixture was diluted with ethyl acetate, and it was washed with 10% sodium thiosulfate, saturated NaHC03and brine. The organic layer was dried over Na2S04, and it was concentrated under reduced pressure. The residue was purified on an ISCO chromatograph (0-10% ethyl acetate/hexane) to give product as a white solid (78 mg, 100%);1H NMR (300 MHz) (CDCb) d 9.86 (s, 1H), 9.23 (bs, 1H), 7.65 (s, 1H), 7.61 (d, J= 9 Hz, 1H), 7.29 (d, j= 9 Hz, 1H), 7.26-7.25 (m, 1H).

923197-75-5 (6-Bromo-1H-indol-2-yl)methanol 13567957, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; TAXIS PHARMACEUTICALS, INC.; LAVOIE, Edmond, J.; SAGONG, Hye Yeon; PARHI, Ajit, K.; (144 pag.)WO2019/99402; (2019); 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.1167055-46-0,4-Bromo-1H-indole-7-carbonitrile,as a common compound, the synthetic route is as follows.

A mixture of 4-bromo-1/-/-indole-7-carbonitrile (1.0 g), Et3N (7.6 mL), and DMAP (55 mg) in DCM (10 mL) was stirred at 0 0C, 4-methylbenzenesulfonyl chloride (2.59 g) was added in one port. After addition completed, the mixture was stirred at 25 0C overnight. Aqueous NaHCO3 solution (20 mL) and DCM (20 mL) were added; the DCM fraction was separated and dried over anhydrous magnesium sulphate. The dried solution was concentrated in vacuum and the resulting residue was purified by Teledyne ISCO (15% EtOAc in Petroleum) to afford 4-bromo-1-[(4- methylphenyl)sulfonyl]-1 H-indole-7-carbonitrile (D3) (1.05 g) as a grey solid. MS (ES): Ci6HnBrN2O2S requires 374.1 (79Br), 376.0 (81Br); found 375.0 (M+H+, 79Br), 377.1 (IVH-H+, 81Br).

1167055-46-0, 1167055-46-0 4-Bromo-1H-indole-7-carbonitrile 53399521, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; GLAXO GROUP LIMITED; LIN, Xichen; REN, Feng; SI, Yugui; WO2010/145203; (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

399-67-7, 7-Fluoro-1H-indole-2-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,399-67-7

To a solution of 7-fluoro-1H-indole-2-carboxylic acid (78 mg, 0.435 mmol), (R)-2- (4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5 -(piperidin-3-yl)benzofuran-3 – carboxamide (100 mg, 0.2 18 mmol) in DCM (1 ml) was added N,N-diisopropylethylamine (169 mg, 1.306 mmol), and the reaction mixture stirred for 5 mm at RT. Then 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (415 mg, 0.653 mmol) was added to the reaction mixture and stirred at RT overnight under N2 protection. The reaction mixture was concentrated under vacuum, then applied onto a silica gel column and eluted with 0-30% MeOH/EtOAc. This resulted in 68 mg (50.3%) of (R)-5-( 1 -(7-fluoro- 1 H-indole-2-carbonyl)piperidin-3-yl)-2-(4-fluorophenyl)-N-methyl-6- (N-methylmethylsulfonamido)benzofiiran-3-carboxamide as white solid. LC-MS (ES, mlz)C32H30F2N4055: 620; Found: 621 [M+H]b.

The synthetic route of 399-67-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; MERCK SHARP & DOHME CORP.; HE, Shuwen; LAI, Zhong; DAI, Xing; XIAO, Dong; LONDON, Clare; ZORN, Nicolas; NARGUND, Ravi; PALANI, Anandan; MCCOMAS, Casey C.; LI, Peng; PENG, Xuanjia; SOLL, Richard; WO2014/205592; (2014); 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

5192-03-0, 1H-Indol-5-amine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4,6-Dichloropyrimidine (5.89 g, 40 mmol), 5-aminoindole (6.27 g, 47 mmol) and N,N-diisopropylethylamine (20.6 ml, 0.12 mol) were dissolved in N-methylpyrrolidone (80 ml), and the reaction mixture was stirred at 50C for 2.5 hours. The reaction mixture was partitioned between ethyl acetate and water; the aqueous layer was subjected to re-extraction with ethyl acetate; and the combined organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure; a small amount of ethyl acetate was added to the residue to crystallize; and the crystals were filtered off, washed with diethyl ether, and dried under aeration to yield the title compound (3.70 g, 15 mmol, 38%) as white crystals. 1H-NMR Spectrum (DMSO-d6) delta (ppm): 6.42 (1H, m), 6.62 (1H, brs), 7.11 (1H, d, J=8.0 Hz), 7.35-7.40 (2H, m), 7.72 (1H, brs), 8.38 (1H, s), 9.68 (1H, s), 11.11 (1H, s)., 5192-03-0

The synthetic route of 5192-03-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Eisai Co., Ltd.; EP1522540; (2005); 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

21296-93-5, 5-Chloro-2,3-dimethyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Organic urea catalyst (2S) -2-[[[[[3,5-bis (trifluoromethyl) phenyl] amino] oxomethyl] amino] -N- (diphenylmethyl) -N, 3,3-trimethylbutyramide (44.8 mg, 0.08 mmol), 2,3-dimethyl-5-chloroindole (71.8 mg, 0.4 mmol), diphenyl phosphate (9.8 mg, 0.04 mmol) and A molecular sieve (199.5 mg) was dissolved in n-hexane (16 mL), and then ethyl trifluoropyruvate (106 muL, 0.8 mmol) was added. The reaction was carried out at room temperature for 42.5 hours. The reaction equation is as follows:The reaction solution was filtered through silica gel, rinsed with ether, and concentrated. Silica gel column chromatography was used to obtain 112 mg of a solid product. The calculated yield was 80%. The measured er value was 93: 7, and n-hexane / dichloromethane (1: 1) was used. ) Recrystallization, mother liquor was concentrated to obtain 100 mg of liquid product, the calculated yield was 72%, and the er value was 96: 4., 21296-93-5

The synthetic route of 21296-93-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Hong Kong University Of Science And Technology Shenzhen Institute; Sun Jianwei; Ma Dengke; (35 pag.)CN110437126; (2019); 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

59908-47-3, 5-Chloro-1-methyl-1H-indole-2-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of 1a (196 mg, 1.00 mmol) in DMF (3.30 mL) were added HOBt·H2O (149 mg, 1.10 mmol), EDCI·HCl (211 mg, 1.10 mmol), 2,2,6,6-tetramethylpiperidin-4-amine (156 muL, 900 mumol) and Et3N (152 muL, 1.10 mmol) at 0 C. The reaction mixture was heated to room temperature and stirred for 20 h. The reaction was quenched with saturated aqueous NaHCO3 solution and extracted with CHCl3. The extract was washed with brine and dried over MgSO4. Concentration under reduced pressure provided the title compound 9a (210 mg, 74% yield) as a white powder., 59908-47-3

The synthetic route of 59908-47-3 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Kobayakawa, Takuya; Ohashi, Nami; Hirota, Yuki; Takahashi, Kohei; Yamada, Yuko; Narumi, Tetsuo; Yoshimura, Kazuhisa; Matsushita, Shuzo; Harada, Shigeyoshi; Tamamura, Hirokazu; Bioorganic and Medicinal Chemistry; vol. 26; 21; (2018); p. 5664 – 5671;,
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