Day: September 10, 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.169674-57-1,5-Chloro-6-fluoro-1H-indole,as a common compound, the synthetic route is as follows.

10 g (68.7 mmol) of 4-chloro-3-fluoro-phenylamine were dissolved in 38 ml dichloro-methane and treated with a solution of 6.82 g (72.1 mmol) of sodium bicarbonate in water (110 ml). At RT 8 ml (103 mmol) of methyl chloroformate were added dropwise over a period of 25 min (temperature rise from 22 to 28 C.). After stirring for 1.5 h at RT, the reaction mixture was diluted with dichloromethane (100 ml). After phase separation, the organic layer was washed with brine (45 ml), dried with magnesium sulfate, filtered and diluted with hexane (140 ml). The dichloromethane was then removed in vacuo and the resulting suspension filtered leading to 13 g (4-chloro-3-fluoro-phenyl)-carbamic acid methyl ester as a white powder (92%). MS (El) 203.1 (M)+.5.34 g (26.2 mmol) of (4-chloro-3-fluoro-phenyl)-carbamic acid methyl ester were dissolved in acetonitrile (50 ml) and treated with 6.49 g (28.85 mmol) of N-iodosuccinimide and 0.23 ml (2.62 mmol) of trifluoromethanesulfonic acid under nitrogen and stirred at RT for 3 hours. The reaction mixture was then poured into 50 ml of saturated sodium bicarbonate solution and extracted twice with ethyl acetate. The combined organic extracts were then washed with brine, dried with magnesium sulfate, filtered and concentrated in vacuo, leading to 8.2 g of (4-chloro-5-fluoro-2-iodo-phenyl)-carbamic acid methyl ester (95%) as a dark blue powder. MS (EI) 328.9 (M)+.153 mg (0.22 mmol) of Pd(PPh3)2Cl2 and 42 mg (0.22 mmol) of CuI were dissolved in 40 ml of triethylamine under argon and the mixture was heated to reflux for 20 min. The reaction mixture was then cooled to 0 C. and 7.2 g (21 mmol) of (4-chloro-5-fluoro-2-iodo-phenyl)-carbamic acid methyl ester were added. After 10 min stirring at RT, 3.45 ml (24.9 mmol) of ethynyltrimethylsilane were added dropwise (exothermic, temperature rise from 18 to 33 C.) and the reaction mixture was stirred for one hour at RT. The mixture was then poured into 180 ml of aqueous 1N HCl and ice and extracted with ethyl acetate. The organic extracts were then washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The remaining crude material (ca 21 mmol) was dissolved in THF (200 ml) and treated with 43.3 ml (43.3 mmol) of tetrabutylammonium fluoride (1M in THF) at RT. After 5 min stirring at RT, the reaction mixture was refluxed for one hour under argon. The reaction mixture was then cooled to RT and concentrated in vacuo. The resulting oil was treated with water (55 ml), stirred for 10 min and finally extracted with ethyl acetate. The combined organic layers were sequentially washed with 1M HCl (50 ml), saturated sodium bicarbonate (50 ml), brine (50 ml) and finally dried with magnesium sulfate, filtered and concentrated in vacuo. The remaining residue was suspended in hexane (200 ml) and-the mixture was heated to reflux, then cooled to 5 C. and the solid was collected by filtration leading to 3.15 g of 5-chloro-6-fluoro-1H-indole as a light brown solid (85%). MS (EI) 169.1 (M)+.35 ml of THF were cooled to -75 C. and 19.05 ml (30.5 mmol) of a 1.6M solution of n-butyllithium in hexane were added under argon. Then a solution of 2.35 g (13.7 mmol) of 5-chloro-6-fluoro-1H-indole in THF (9 ml) was added dropwise (temperature kept between -70 and -75 C.) over 15 min. After 5 additional min of stirring at this temperature a solution of 3.7 g of potassium tert-butylate in THF (15 ml) was added over period of 10 min (temperature kept between -70 and -75 C.). The resulting brown solution was then stirred for 2 hours at the same temperature and treated with a large excess of solid CO2. The temperature was then raised to 10 C. over a period of 75 min and water (30 ml) was added to the reaction mixture. After separation of the organic layer, the aqueous layer was extracted with ether and treated with concentrated HCl to adjust the pH to 1. The resulting suspension was then filtered and the solid was washed with water and dried in high vacuo. The remaining residue was suspended in 10 ml of hexane/ether 9:1 and stirred for 15 min, filtered off, washed with 5 ml of the same solvent mixture and was dried in high vacuo, leading to 2.2 g of 5-chloro-6-fluoro-1H-indole-7-carboxylic acid as a light brown solid (75%). MS: 212.2 (M-H)-

169674-57-1, The synthetic route of 169674-57-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Faeh, Christoph; Kuehne, Holger; Luebbers, Thomas; Mattei, Patrizio; Maugeais, Cyrille; Pflieger, Philippe; US2007/185113; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.74420-02-3,4-Hydroxy-7-azaindole,as a common compound, the synthetic route is as follows.,74420-02-3

A solution of 1 ,2,3-trifluoro-5-nitrobenzene (CAS No. [66684-58-0]; 3.59 g, 20.3 mmol) and 1 H- pyrrolo[2,3-b]pyridin-4-ol (CAS No. [74420-02-3]; 1 .10 eq., 2.99 g, 22.3 mmol) in DMSO (65 mL) was treated with potassium carbonate (4.00 eq, 1 1 .2 g, 81.1 mmol) and stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate (500 mL) and washed with water (3 x 200 mL) and brine (150 mL), dried with sodium sulfate and concentrated in vacuo. The obtained material was purified by flash chromatography (S1O2- hexane/ ethyl acetate) to give the title compound (3.1 g, 52percent). LC-MS (method 2): Rt = 1 .13 min; MS (ESIpos): m/z = 292 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) delta [ppm] = 6.35 (d, 1 H), 6.59 (d, 1 H), 7.47 (d, 1 H), 8.13 (d, 1 H), 8.37 – 8.43 (m, 2H), 1 1 .97 (br s, 1 H).

As the paragraph descriping shows that 74420-02-3 is playing an increasingly important role.

Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; DEUTSCHES KREBSFORSCHUNGSZENTRUM HEIDELBERG; BAYER AKTIENGESELLSCHAFT; BUCHMANN, Bernd; SCHMEES, Norbert; MOWAT, Jeffrey Stuart; LEDER, Gabriele; PANKNIN, Olaf; CARRETERO, Rafael; AIGUABELLA FONT, Nuria; BRIEM, Hans; FRIBERG, Anders Roland; HUSEMANN, Manfred; BOeMER, Ulf; STOeCKIGT, Detlef; NEUHAUS, Roland; BERNDT, Sandra; PETERSEN, Kirstin; OFFRINGA, Rienk; (494 pag.)WO2018/228920; (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

24985-85-1, Ethyl 5-hydroxyindole-2-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 5-hydroxyindole-2-carboxylic acid ethyl ester (14.2 g, 68.5 mmol) in DMF (150 mL) was added cesium carbonate (26.8 g, 82.3 mmol). The resulting mixture was stirred at room temperature for 20 min followed by the addition of allyl bromide (5.94 mL, 68.5 mmol). The reaction mixture was stirred at room temperature for 24 h. The reaction was diluted with ethyl acetate, washed with H2O, brine and dried (Na2SO4). The solvent was removed in vacua and the resulting crude product was purified by flash column chromatography on silica gel (0-20% EtOAc/hexanes) to give the desired material as solid (8.9 g, 52%). LC/MS (ES+) m/e 248 [M+H]+.

24985-85-1, 24985-85-1 Ethyl 5-hydroxyindole-2-carboxylate 90677, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; SmithKline Beecham Corporation; US6670388; (2003); B1;,
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

10242-01-0, 5-Methoxy-1H-indole-3-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

10242-01-0, General procedure: 60% NaH (0.91 g, 22.8 mmol) was added in portions to a solution of 1b-h (11.2 mmol) in dry DMF (35 mL) at 0-5 C. After addition, the mixture was stirred for 30 min. Iodomethane (33.6 mmol) was then added at 0-5 C and stirred for 2 h at room temperature. The mixture was then poured into H2O (120 mL) and the resulting solution was extracted with ethyl acetate (50 mL ¡Á 3). The organic phase was combined and washed with brine (150 mL ¡Á 3), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by flash column chromatography on silica gel to afford 2b-h.

As the paragraph descriping shows that 10242-01-0 is playing an increasingly important role.

Reference£º
Article; Hu, Yuanyuan; Ruan, Wenchen; Gao, Anhui; Zhou, Yubo; Gao, Lixin; Xu, Meng; Gao, Jianrong; Ye, Qing; Li, Jia; Pang, Tao; Pharmazie; vol. 72; 12; (2017); p. 707 – 713;,
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

101774-27-0, 6-Bromo-1H-indole-3-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a 250 mL round bottom Hask was added 6-bromo-l H-indole-3-carboxylic acid ASa(5 g, 20.83 mmol, 1.0 equiv.), N,N-dimethylformamide (150 mL), Mel (5.9 g), andsodium hydride (3.5 g, 145.83 mmol, 7.0 equiv.). The resulting mixture ‘.Vas stirred at 10-25 oc for l h, a.nd then diluted with 1500 mL ofH?O. The aqueous mixture was extracted15 with ethyl acetate (200 mL x 3) and the combined organic layers were dried over anhydrousmagnesium sulfate, filtered, and concentrated in vacuo. The cmde product was purified byre-crystallization from PE. The solids were collected by filtration to yield 3.5 g (63%) ofmethyl 6-brorno-l-methyl-l H-indole-3-carboxylate A-8b a.s a light yellow solid.

101774-27-0, The synthetic route of 101774-27-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1201-26-9,3-Indolylacetone,as a common compound, the synthetic route is as follows.

[0570] Asymmetric reduction applying transaminase TA-P2-A07 was performed in buffer; iso-propyl amine and organic co-solvents such as DMSO or Acetonitrile on 5 g scale. Compound (XXI) was converted to compound (3) as described herein at a degree above 95% with an enantiomeric excess (EE) above 99% after 1 day.

1201-26-9, As the paragraph descriping shows that 1201-26-9 is playing an increasingly important role.

Reference£º
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CHUNG, Cheol Keun; XU, Jie; IDING, Hans; CLAGG, Kyle; DALZIEL, Michael; FETTES, Alec; GOSSELIN, Francis; LIM, Ngiap-Kie; ZHANG, Haiming; CHAKRAVARTY, Paroma; NAGAPUDI, Karthik; ROBINSON, Sarah; (241 pag.)WO2019/245974; (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

902772-13-8, 5-Bromo-1H-indole-2-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

902772-13-8, Anhydrous CH2Cl2 (270 mL), Et3N (4.86 mL, 34.7 mmol) and pyridine (2.82 mL, 34.7 mmol) were added to 5-bromoindole-2-carbom’trile (3.83 g, 17.3 mmol; see step (b) above), Cu(OAc)2 (6.29 g, 34.7 mmol), 3 A molecular sieves (ca. 7 g) and4-cyclopentyloxyphenylboronic acid (7.15 g, 34.7 mmol). The mixture was stirred vigorously at rt for 72 h and filtered through Celite. The solids were washed withEtOAc, and the combined filtrates concentrated and purified by chromatography to afford the sub-title compound (3.87 g, 59%).

902772-13-8 5-Bromo-1H-indole-2-carbonitrile 68473340, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; BIOLIPOX AB; WO2006/77367; (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

942-26-7, 5-Chlorotryptamine hydrochloride is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

942-26-7, General procedure: Commercial tryptamine hydrochloride (4.9 g, 24.9 mmol, 1 eq) and glyoxylic acid (2.6 g, 27.4 mmol, 1.1 eq) were dissolved in 78 mL H2O,and then the solution of KOH (1.38 g, 24.9 mmol, 1 eq) in 6 mL H2O was added dropwise. The mixture was stirredfor 1h and the white precipitate was collected by filtration. The precipitate was dissolved in 78 mL H2O and thesolution was added conc. HCl (6.6 mL) at room temperature. After stirring for one hour under reflux, the solutionwas added 6.6 mL conc. HCl again and stirred for another 0.5 h under reflux. After cooling to r.t., the light-greencrystal was obtained and collected by filtration and then dissolved in 78 mL H2O. The solution was basified by 20%KOH until pH > 13, and the white precipitate was filtered off and washed with water three times to the titlecompound S16a (3.1 g, 73%).

942-26-7 5-Chlorotryptamine hydrochloride 2827494, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Article; Zheng, Hongbo; Li, Lin; Sun, Bin; Gao, Yun; Song, Wei; Zhao, Xiaoyu; Gao, Yanhui; Xie, Zhiyu; Zhang, Nianzhao; Ji, Jianbo; Yuan, Huiqing; Lou, Hongxiang; European Journal of Medicinal Chemistry; vol. 150; (2018); p. 30 – 38;,
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.348640-06-2,4-Bromo-7-azaindole,as a common compound, the synthetic route is as follows.

348640-06-2, A solution of 4-bromo-1H-pyrrolo[2,3-b]pyridine (10.0 g, 0.0508 mol) in DMF (40 mL) was cooled under nitrogen to 0 C. Sodium hydride (3.0 g, 0.075 mol) was added portionwise. The reaction was stirred for 1 hour. To this mixture, [2-(trimethylsilyl)ethoxy]methyl chloride (10.8 mL, 0.061 mol) was added slowly. After being stirred at 0 C. for 1 hour, the reaction was quenched with water and extracted with EtOAc twice. The combined extracts were washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with 0-25% EtOAc/hexanes to afford 15.7 g (94.5%) of the desired product as a yellowish oil. LC/MS found: 327.1, 329.1 (M+H)+.

As the paragraph descriping shows that 348640-06-2 is playing an increasingly important role.

Reference£º
Patent; Huang, Taisheng; Xue, Chu-Biao; Wang, Anlai; Kong, Ling Quan; Ye, Hai Fen; Yao, Wenqing; Rodgers, James D.; Shepard, Stacey; Wang, Haisheng; Shao, Lixin; Li, Hui-Yin; Li, Qun; US2011/224190; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.143612-79-7,3-(4-Chlorobutyl)-1H-indole-5-carbonitrile,as a common compound, the synthetic route is as follows.

6-(2-(Piperazin- 1 -yl)pyrimidin-5-yl)nicotinamide dihydrochloride (400 mg, 1.12 mmol), 3-(4-chlorobutyl)-1H-indole-5-nitrile (312 mg, 1.34 mmol), anhydrous sodium carbonate (712 mg, 6.72 mmol) and sodium iodide (50 mg, 0.33 mmol) were added into anhydrous acetonitrile (15 mL) in turn. The solution was heated to 90 C and reacted for 36 hours. The reaction was stopped, and the mixture was cooled to room temperature. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (dichloromethane/methanol (v/v) = 20/1) to give the title compound as a faint yellow solid (465 mg, 86.4%).MS (ESI, pos. ion) m/z: 481.30 [M+H].?H NIVIR (400 1?IFlz, DMSO-d6) (ppm): 11.36 (s, 1H), 9.08 (s, 2H), 9.04 (d, J= 1.7 Hz,1H), 8.26 (dd, J= 8.3, 2.1 Hz, 1H), 8.14 (s, 1H), 8.10 (s, 1H), 8.05 (d, J= 8.3 Hz, 1H), 7.52 (s,1H), 7.49 (d, J= 8.3 Hz, 1H), 7.40 (dd, J= 8.4, 0.9 Hz, 1H), 7.35 (s, 1H), 3.90 (brs, 4H), 3.39(brs, 4H), 2.73 (t, J 7.4 Hz, 2H), 2.452.39 (m, 2H), 1.731.65 (m, 2H), 1.54 (d, J= 6.7 Hz,2H);HPLC: 95.11%.

143612-79-7, 143612-79-7 3-(4-Chlorobutyl)-1H-indole-5-carbonitrile 9881123, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; SUNSHINE LAKE PHARMA CO., LTD.; JIN, Chuanfei; ZHONG, Wenhe; LIANG, Haiping; ZHANG, Yingjun; (79 pag.)WO2019/62662; (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