Tag: M.W:100-200

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

To a solution of 7-fluoro-1H-indole-2-carboxylic acid (78 mg, 0.435 mmol), (5)- 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 (169mg, 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 78 mg (58%) of (S)-5-( 1 -(7-fluoro- 1 H-indole-2-carbonyl)piperidin-3 -yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3 -carboxamide as white solid. LC-MS (ES, mlz) C32H30F2N4055: 620; Found: 621 [M+H].

399-67-7, As the paragraph descriping shows that 399-67-7 is playing an increasingly important role.

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; WO2014/209729; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.39689-58-2,2-(1H-Indol-6-yl)acetic acid,as a common compound, the synthetic route is as follows.

Hydroxybenzotriazole (614 mg, 4.5 mmol), 4-ethylmorpholine (320 mul, 2.5 mmol), propargylamine (160 mul, 2.5 mmol) and 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide hydrochloride (523 mg, 2.7 mmol) were added to an ice cold solution of (1H-indol-6-yl)-acetic acid (640 mg, 2.2 mmol; U.S. Pat. No. 4,894,386 A) in tetrahydrofuran (6.4 ml). The solution was naturally warmed to ambient temperature and stirred for 14 h. Ice water/brine 1/1 was added and the mixture was extracted two times with dichloromethane. The combined extracts were successively washed with 1 N HCl, brine, 1 N NaOH and brine, and dried over sodium sulfate. The solvent was removed under reduced pressure to give brown crystals which were recrystallized from heptane/dichloromethane to give 380 mg (1.8 mmol, 80%) of the title compound as colorless crystals. MS: 213.4 (M+H)+., 39689-58-2

39689-58-2 2-(1H-Indol-6-yl)acetic acid 14882503, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Ackermann, Jean; Aebi, Johannes; Binggeli, Alfred; Grether, Uwe; Kuhn, Bernd; Maerki, Hans-Peter; Meyer, Markus; US2006/35956; (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

2795-41-7, 6-Fluoroindole-3-carboxaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2 g of intermediate I-1 and 6 g of ethoxycarbonyl methylene triphenylphosphine are dissolved in 50 ml of dry acetonitrile.70 overnight.TLC showed complete conversion of the substrate.Stop the reaction,The reaction was cooled to room temperature.Add 50ml ethyl acetate and 50ml water,Extraction and separation of water layer,The organic layer is dry,concentrate,Column chromatography gave 6.1 g of intermediate I-17 (white solid, yield 85%).

2795-41-7, 2795-41-7 6-Fluoroindole-3-carboxaldehyde 262903, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Hu Youhong; Geng Meiyu; Xing Weiqiang; Ding Jian; Ai Jing; (86 pag.)CN103664895; (2018); B;,
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.61019-05-4,5-Methoxy-7-methyl-1H-indole,as a common compound, the synthetic route is as follows.

61019-05-4, Oxalyl chloride (0.17 mL, 1.93 mmol) was added dropwise via syringe over 1 min to DMF (1.5 mL) in a vial charged with a magnetic stir bar under N2 at 0 C. After ~30 min, 5-methoxy-7-methyl-1H-indole (342 mg, 2.123 mmol) was added dropwise via syringe over ~30 s as a solution in DMF (2 mL). The reaction was allowed to warm to room temperature and stir overnight, after which 1 N NaOH (2 mL) was added dropwise via syringe over 30 s. The reaction was then heated to 100 oC for 20 min, after which it was cooled to room temperature. After 28 h of total reaction time, the mixture was diluted with H2O (15 mL) and DCM (20 mL). The organic layer was separated, and the aqueous layer was washed with DCM (10 mL). The combined organic layers were washed with H2O (2 × 15 mL) and brine (10 mL), dried with Na2SO4, filtered, and concentrated in vacuo to provide a dark red crude residue. The crude material was purified via flash chromatography on silica (24 g column, 0-60% EtOAc/heptane) to afford 300 mg (82% yield) of 13 as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 12.27 – 11.84 (m, 1H), 9.89 (s, 1H), 8.20 (d, J = 3.30 Hz, 1H), 7.41 (d, J = 2.45 Hz, 1 H), 6.71 (dd, J = 2.32, 0.73 Hz, 1H), 3.76 (s, 3H), 2.48 – 2.43 (m, 3H); LCMS m/z = 190.2 ([M+H]+), tR = 1.00 min (method A).

The synthetic route of 61019-05-4 has been constantly updated, and we look forward to future research findings.

Reference：
Article; DeChristopher, Brian; Park, Soo-Hee; Vong, Linh; Bamford, Derek; Cho, Hyun-Hee; Duvadie, Rohit; Fedolak, Allison; Hogan, Christopher; Honda, Toshiyuki; Pandey, Pramod; Rozhitskaya, Olga; Su, Liansheng; Tomlinson, Elizabeth; Wallace, Iain; Bioorganic and Medicinal Chemistry Letters; vol. 29; 8; (2019); p. 991 – 994;,
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.5192-03-0,1H-Indol-5-amine,as a common compound, the synthetic route is as follows.

Intermediate-1: N-(lH-indol-5-yl)pivalamideTo a stirred solution of 5-Indole amine (0.6 g, 4.54 mmol) in anhydrous dichloromethane (15 mL), triethylamine (1.3 mL, 9.0 mmol) and pivaloyl chloride (0.45 mL, 5.4 mmol) were added and stirred at room temperature for 2 h. The reaction mixture was diluted with water; the organic layer was separated and concentrated in vacuo. The resultant residue was purified by flash column chromatography to give N-(lH-indol-5-yl)pivalamide (0.88g, 89%); MS: 217.0 (M+l).

5192-03-0, As the paragraph descriping shows that 5192-03-0 is playing an increasingly important role.

Reference：
Patent; LUPIN LIMITED; THOTAPALLY, Rajesh; KACHI, Onkar, Gangaram; RODGE, Atish, Harishchandra; PATHAK, Ashok, Bhau; KARDILE, Bhavana, Shrirang; SINDKHEDKAR, Milind, Dattatraya; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; WO2012/69917; (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

399-51-9, 6-Fluoro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Oxalyl chloride (0.3 mL) was added in a drop-wise manner to cooled (ice-bath) DMF (3 mL) under stirring. The mixture was then stirred at 0 C for 1 h. A solution of the substituted indole (4 mmol) in DMF (1.5 mL) was then added to the reaction mixture in a dropwise manner. The resulting mixture was stirred at room temperature for 5 h. A 2 N solution of sodium hydroxide (2 mL) was then added, and the mixture was heated at 100 C for 10 min. The mixture was then cooled and extracted with ethyl acetate (3 X 50 mL). The organic layers were combined and washed with sequentially water and brine. The organics were dried (Na2SO4) and distilled to dryness to give the crude residue, which was purified by flash column chromatography using ethyl acetate/petroleum ether (3:1, v/v) as the eluent to give pure indole-3-carbaldehyde (4a-k).

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

Reference：
Article; Zheng, Jing; Deng, Lijuan; Chen, Minfeng; Xiao, Xuzhi; Xiao, Shengwei; Guo, Cuiping; Xiao, Gaokeng; Bai, Liangliang; Ye, Wencai; Zhang, Dongmei; Chen, Heru; European Journal of Medicinal Chemistry; vol. 65; (2013); p. 158 – 167;,
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.81779-27-3,4-Hydroxy-1H-indole-3-carbaldehyde,as a common compound, the synthetic route is as follows.,81779-27-3

EXAMPLE 2 OF REFERENCE 3-Formyl-4-hydroxyindole-1-carboxylic Acid tert-butyl Ester (2-1) (R7=R11=H) A mixture of the 3-formyl-4-hydroxyindole (1-1) 323 mg, di-tert-butyldicarbonate 458 mg, dimethylaminopyridine 12.5 mg and acetonitrile 25 ml was stirred under cooling in ice for 3 h.The solvent was removed under reduced pressure and the residue obtained was recrystallized from acetone-isopropyl ether to give the titled compound as pale yellow crystals, m.p. 159-161 C.(dec.), 389 mg.Yield 74%. 1H-NMR(CDCl3): 1.71 (9H, s), 6.84 (1H, dd, J=8.1, 0.9 Hz), 7.31 (1H, t, J=8.1 Hz), 7.61 (1H, dd, J=8.1, 0.9 Hz), 8.25 (1H, s), 9.76 (1H, d, J=0.6 Hz), 10.13 (1H, s).

81779-27-3 4-Hydroxy-1H-indole-3-carbaldehyde 9815282, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Fukui, Yoshikazu; Adachi, Makoto; Sasatani, Takashi; US2003/236295; (2003); 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.90924-06-4,1-Methyl-4-indolecarboxylic Acid,as a common compound, the synthetic route is as follows.

90924-06-4, Oxalyl chloride (1.55 mL, 18.3 mmol) was added to a suspensionof the above acid (2.48 g, 15.3 mmol) in DCM (100 mL, anhydrous)and DMF (0.05 mL, 0.64 mmol) at 20 C. The mixture wasstirred at 20 C for 1 h to give a colourless solution which wascooled to 0 C. N,O-Dimethylhydroxylamine hydrochloride (1.64g, 16.8 mmol) and pyridine (3.71 mL, 45.9 mmol) were addedsequentially and the mixture was stirred at 20 C for 18 h, thenpartitioned between EtOAc and sat. aq. NaHCO3. Column chromatographywith 95:5 DCM:EtOAc gave N-methoxy-N-methylbenzofuran-5-carboxamide (2.28 g, 73%) as a pale brown oil. 1H NMR(CDCl3) d 7.99 (d, J = 1.4 Hz, 1H), 7.65-7.69 (m, 2H), 7.52 (dt, J =8.6, 0.6 Hz, 1H), 6.82 (dd, J = 2.2, 0.9 Hz, 1H), 3.56 (s, 3H), 3.39 (s,3H). Found: [M+H] = 206.2.

90924-06-4 1-Methyl-4-indolecarboxylic Acid 14987287, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Sutherland, Hamish S.; Tong, Amy S.T.; Choi, Peter J.; Conole, Daniel; Blaser, Adrian; Franzblau, Scott G.; Cooper, Christopher B.; Upton, Anna M.; Lotlikar, Manisha U.; Denny, William A.; Palmer, Brian D.; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 1797 – 1809;,
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.6127-17-9,6-Chloro-2-methyl-1H-indole,as a common compound, the synthetic route is as follows.,6127-17-9

To a solution of 0.38 g (2.3 mmol) 6-chloro-2-methyl-1H-indole in 20 ml 1,2-dichloroethane at 0 C. were added 0.35 ml (2.5 mmol) trifluoroacetic anhydride. The reaction mixture was quenched with aqueous 2 M sodium carbonate solution after 30 min and extracted with dichloromethane (3*100 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give the title compound (0.57 g; 95%) as an off-white solid. MS m/e (%): 260 (M-H+, 100).

As the paragraph descriping shows that 6127-17-9 is playing an increasingly important role.

Reference：
Patent; Bissantz, Caterina; Grundschober, Christophe; Masciadri, Raffaello; Ratni, Hasane; Rogers-Evans, Mark; Schnider, Patrick; US2008/161315; (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

10601-19-1, 5-Methoxy-1H-indole-3-carbaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 5-methoxyindole-3-carboxaldehyde (80 g) in dimethylformamide (1 L) under nitrogen was treated portion-wise with sodium hydride (20.1 g, 60% dispersion in mineral oil) over 15 minutes. After stirring at ambient temperature for 30 minutes the mixture was treated dropwise with methyl iodide (31.3 mL) over 10 minutes and stirring was then continued for a further 2 hours. The reaction mixture was poured cautiously into water then extracted with ethyl acetate. The organic phase was washed with water, then dried over sodium sulfate and then evaporated. The residue was triturated with pentane to give the title compound (76 g) as a pale brown solid, m.p. 133-134 C. 1H NMR [(CD3)2SO]: delta 9.86 (1H, s); 8.20 (1H, s); 7.60 (1H, d, J=2.6 Hz); 7.50 (1H, d, J=8.9 Hz); 6.96 (1H, dd, J=8.9 and 2.6 Hz); 3.86 and 3.80 (6H, s)., 10601-19-1

10601-19-1 5-Methoxy-1H-indole-3-carbaldehyde 82758, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Cox, Paul J.; Majid, Tahir N.; Lai, Justine Y.Q.; Morley, Andrew D.; Amendola, Shelley; Deprets, Stephanie D.; Edlin, Christopher; US2004/9983; (2004); 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