Downstream synthetic route of 50820-65-0

50820-65-0 Methyl 1H-indole-6-carboxylate 639844, aindole-building-block compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.50820-65-0,Methyl 1H-indole-6-carboxylate,as a common compound, the synthetic route is as follows.,50820-65-0

To a solution of methyl 1H-indole-6-carboxylate (17.5 g, 99.9 mmol, 1.0 eq) in i-PrOH (200 mL) was added cyclopent-2-en-1-one (16.4 g, 199.8 mmol, 16.7 mL, 2.0 eq) and SnCl2*2H2O (2.25 g, 9.99 mmol, 831.8 muL, 0.1 eq) under N2. After addition, the mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated and diluted with DCM (250 mL). The organic layer was separated and washed with H2O (200 mL), brine (200 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2) to give compound 03-4-1 (22.4 g, 79percent yield).1H NMR (CDCl3, 400 MHz): delta 8.38 (s, 1 H) 8.17 (s, 1 H) 7.84 (d, J=8.8 Hz, 1 H) 7.66 (d, J=8.8 Hz, 1 H) 7.19 (d, J=2.01 Hz, 1 H) 3.97 (s, 3 H) 3.74-3.77 (m, 1 H) 2.77-2.83 (m, 1 H) 2.58-2.59 (m, 1 H) 2.39-2.48 (m, 3 H) 2.15-2.17 (m, 1 H).

50820-65-0 Methyl 1H-indole-6-carboxylate 639844, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; KYRAS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; (587 pag.)WO2017/96045; (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

Brief introduction of 50820-65-0

As the paragraph descriping shows that 50820-65-0 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.50820-65-0,Methyl 1H-indole-6-carboxylate,as a common compound, the synthetic route is as follows.

50820-65-0, A mixture of methyl lH-indole-6- carboxylate (1.75 g, 10 mmol) and NaH (0.52 g, 13 mmol, 60percent in oil) in THF (20 mL) was stirred at r.t. for 30 min, followed by addition of a solution of 4-methylbenzene-l-sulfonyl chloride (2.85 g, 15 mmol) in THF (5 mL). The reaction mixture was stirred at r.t. for another lhr, then quenched with water and extracted with EtOAc. The combined organic layers were dried over anhydrous Na2SC>4 and concentrated under reduced pressure. The residue was purified by column chromatography to give the desired product (2.8 g, 85percent yield).LCMS: m/z 330 (M+H)+.

As the paragraph descriping shows that 50820-65-0 is playing an increasingly important role.

Reference£º
Patent; SPERO THERAPEUTICS, INC.; ZAHLER, Robert; (262 pag.)WO2016/112088; (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

Some tips on 50820-65-0

The synthetic route of 50820-65-0 has been constantly updated, and we look forward to future research findings.

50820-65-0, Methyl 1H-indole-6-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,50820-65-0

Example 1; Preparation of (2E)-3-{4-[({1-[({3-CycIohexyl -1-[2- (dimethylamino) – 2-oxoethyl -2-phenyl-1H-indol-6-yl}carbonyl)amino]cyclopenthyl}carbonyl) amino]phenyl }acrylic acid; Step 1; 3-Cyclohex-1-en-1-yl-1H-indole-6-carboxylic acid; To a solution of methyl-indole-6-carbochiylate in MeOH (1,7 M) was added cyclohexanone (3.0eq.) followed by 30percent NaOMe in MeOH (6,0 eq.) in 100 ml portions over 20 min. The resulting mixture was stirred at RT for 45 min and relaxed for 8 h. Water was added, and the mixture stirred at RT until all solids had dissolved. The organic solvent was removed under vacuum and the pH of the aqueous phase adjusted to 1, by slow addition of concentrated HCl at 0 ¡ãC. The precipitate was isolated by filtration, and then washed with water, until the pH of the water reached 6- 7, Drying under high vacuum gave the title compound as a beige solid (100percent),

The synthetic route of 50820-65-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI SPA; WO2006/29912; (2006); 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

Downstream synthetic route of 50820-65-0

50820-65-0 Methyl 1H-indole-6-carboxylate 639844, aindole-building-block compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.50820-65-0,Methyl 1H-indole-6-carboxylate,as a common compound, the synthetic route is as follows.

50820-65-0, To a solution of methyl 1H-indole-6-carboxylate (124 g, 708 mmol) in tetrahydrofuran (500 ml) was added 4-dimethylaminopyridine (865 mg, 7 mmol). Then, a solution of di-tert-butyl dicarbonate (156 g, 715 mmol) in tetrahydrofuran (150 ml) was added dropwise at room temperature over about 1 hr, and the mixture was stirred for 1 hr. The reaction mixture was concentrated, and the residue was purified by silica gel chromatography to give the title compound (193 g, yield 99percent).1H-NMR (400 MHz, DMSO-d6) delta: 1.65 (9H, s), 3.89 (3H, s), 6.82H, dd, J=3.63, 0.86 Hz), 7.74 (1H, d, J=8.06 Hz), 7.85 (1H, dd, J=8.06, 0.86 Hz), 7.87 (1H, d, J=3.63 Hz), 8.76 (1H, d, J=0.81 Hz).

50820-65-0 Methyl 1H-indole-6-carboxylate 639844, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; JAPAN TOBACCO INC.; US2011/306599; (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

Some tips on 50820-65-0

The synthetic route of 50820-65-0 has been constantly updated, and we look forward to future research findings.

50820-65-0, Methyl 1H-indole-6-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

50820-65-0, To a DMF (60 mL) solution of methyl 1H-indole-6-carboxylate (5.1 g, 29.1 mmol) at -60 C was added a DMF solution (40 mL) of NBS (5.70 g, 32.0 mmol)dropwise. The reaction mixture was stirred for 2 hours while it was warmed up to room temperature. The reaction mixture was then poured into ice water (1 L) and the precipitate formed was collected through via vacuum filtration. The solid was washed with water. The solid was dissolved in ethyl acetate and washed twice with sat. aq. NaC1. The ethyl acetate layer was separated, dried (Na2504), filtered andconcentrated to give the cmde product. The material was carried on without further purification. LCMS (ESI) m/e 254.1 [(M+H), calcd C10H9Br1N1O2, 253.91; LC/MS retention time (method A): IR = 1.63 mm.

The synthetic route of 50820-65-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; LUO, Guanglin; CHEN, Ling; (83 pag.)WO2017/184658; (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

Simple exploration of 50820-65-0

50820-65-0 Methyl 1H-indole-6-carboxylate 639844, aindole-building-block compound, is more and more widely used in various fields.

50820-65-0, Methyl 1H-indole-6-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Compound 2 (5 mmol) was added to hydrazine- hydrate (80) (3 mL)at room temperature, and the mixture was irradiated continually for 5-8 min at 300 W. The reaction progress was monitored by TLC. After the reaction was complete and the mixture was sufficiently cooled, intermediate 3 (yield 83-98) was formed., 50820-65-0

50820-65-0 Methyl 1H-indole-6-carboxylate 639844, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Article; Ye, Ying; Suo, Yourui; Yang, Fang; Yang, Yongjing; Han, Lijuan; Journal of Chemical Research; vol. 39; 5; (2015); p. 296 – 299;,
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

Analyzing the synthesis route of 50820-65-0

As the paragraph descriping shows that 50820-65-0 is playing an increasingly important role.

50820-65-0,50820-65-0, Methyl 1H-indole-6-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of compound 26 (2 g, 11.4 mmol) and cyclohexanone (3.36 g,34.2 mmol) in MeOH (15 mL), aqueous KOH (1.92 g, 34.2 mmol, dissolved in 13 mL water) was added. The resulting reaction mixture was stirred at 75 ¡ãC for 18 h. The progress of the reaction was monitored by LCMS. After completion, the reaction mixture was concentrated in vacuo. The residue was diluted with water, acidified with acetic acid pH?6; the obtained solidwas filtered; washed with water and dried in vacuo to afford the crude. The crude compound was triturated with IPA to afford compound 34 (1.6 g, 58percent) as light brown solid. ?H-NMR (400 MHz, DMSO-d6): oe 11.33 (s, 1H), 7.97 (s, 1H), 7.75 (d, J= 8.0 Hz, 1H), 7.61 (d, J= 8.4 Hz, 1H), 7.47 (s, 1H), 6.19 (s, 1H), 2.42 ?2.39 (m, 2H), 2.22 ? 2.20 (m, 2H), 1.76 – 1.72 (m, 4H). LCMS observed (m/z): 242 (M+1).

As the paragraph descriping shows that 50820-65-0 is playing an increasingly important role.

Reference£º
Patent; ASSEMBLY BIOSCIENCES, INC.; TURNER, William; ARNOLD, Lee, Daniel; LI, Leping; BURES, Mark; HAYDAR, Simon; MAAG, Hans; BANNEN, Lynne; (176 pag.)WO2018/53157; (2018); 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