Category: 59908-47-3

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

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: Version B: 780 mg of 1 d and 1747 mg of HATU were first dissolved in 10 ml DMSO. Next, 314 mg of 2-methoxyethylamine and 1080 mg of N,N-diisopropylethylamine were added. The mixture was stirred for 1 hr at RT. The reaction mixture was poured into water and extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated. The residue was purified chromatographically on the Biotage SP4. Gradient: ethyl acetate/methanol 0-10%. Yield: 740 mg of the title compound. Analogously to Example 1b, Version B, 43 mg of the title compound was obtained from 100 mg of 71a and 89 mg of 5-chloro-1-methyl-1H-indol-2-carboxylic acid in DMF. 1H-NMR (400 MHz, DMSO-d6): delta [ppm], 1.29 (2H), 1.38-1.72 (2H), 2.26-2.43 (1H), 2.54 (3H), 2.71-3.21 (2H), 3.73 (3H), 3.84-4.18 (3H), 4.38 (3H), 6.59 (1H), 7.15-7.28 (2H), 7.47 (1H), 7.55 (1H), 7.65 (1H), 8.57 (1H), 8.83 (1H)., 59908-47-3

59908-47-3 5-Chloro-1-methyl-1H-indole-2-carboxylic acid 931711, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; LlNDENTHAL, Bernhard; BRAeUER, Nico; SERNO, Peter; ROTGERI, Andrea; FUHRMANN, Ulrike; BUCHMANN, Bernd; MENGEL, Anne; ROeHN, Ulrike; TER LAAK, Antonius; (221 pag.)US2016/89364; (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

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,59908-47-3

Production Example 5-4tert-butyl 6-{[5-chloro-1-methyl-1H-indol-2-yl]carbonyl}amino)octahydroisoquinoline-2(1H)-carboxylate To a methanol solution (100 mL) of the compound obtained in Production example 5-3 (3.3 g), 10% palladium carbon (500 mg) was added, and the resulting solution was stirred overnight at room temperature under 1 atm hydrogen atmosphere. The reaction solution was filtered and the filtrate was concentrated under reduced pressure. To a DMF (70 mL) solution of the residue, commercially available 5-chloro-1-methyl-1H-indole-2-carboxylic acid (2.4 g), HATU (4.4 g) and subsequently diisopropylethylamine (4.1 mL) were added, and the resulting solution was stirred overnight at room temperature. Water was added to the reaction solution, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:2), whereby the title compound (3.2 g) was obtained as a single optically active isomer (the arrangement in the structural formula is a relative configuration).

As the paragraph descriping shows that 59908-47-3 is playing an increasingly important role.

Reference：
Patent; MSD K.K; US2012/28990; (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.59908-47-3,5-Chloro-1-methyl-1H-indole-2-carboxylic acid,as a common compound, the synthetic route is as follows.

59908-47-3, Step 3: Synthesis of 5-chloro-l-methyl-N-{4-[(pyrimidin-2-yl)({[2- (trimethylsilyl)ethoxy] methyl})sulfamoyl]phenyl}-lH-indole-2-carboxamide 43.3 [00511] To a solution of 5-chloro-l-methyl-lH-indole-2-carboxylic acid (43.2, 81 mg, 0.39 mmol) in MeCN (dry, 5ml) was added 4-amino-N-phenyl-N-{[2- (trimethylsilyl)ethoxy]methyl}benzene-l-sulfonamide (150 mg, 0.4 mmol) and 3-picoline (57 mu, 0.58 mmol). To this solution was added methanesulfonyl chloride (36 mu, 0.46 mmol) and the mixture was stirred under nitrogen at rt. After 60h the solvent was removed in vacuo and the crude material purified by flash column chromatography (heptane/EtOAc 80/20 to 60/40) to obtain 97 mg (43%) of 5-chloro-l-methyl-N-{4-[(pyrimidin-2-yl)({[2- (trimethylsilyl)ethoxy]methyl})sulfamoyl]phenyl}-lH-indole-2-carboxamide 43.3 as a white powder.

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

Reference：
Patent; RAZE THERAPEUTICS, INC.; SAIAH, Eddine; (148 pag.)WO2016/40449; (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