Category: indole-building-block

31241-19-7, 5-Methoxy-2,3,3-trimethyl-3H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

31241-19-7, General procedure: In parallel, substituted hydrazines 1 (4.0 g, 22.25 mmol) were reacted with 3-methylbutanone(3 mL, 28.04 mmol) in acetic acid and heated to a 100 C for 24 h. The solution was then neutralizedusing sodium bicarbonate and extracted using dichloromethane; affording substituted indolenineheterocycles 2 which was dried under reduced pressure. The heterocycles 2 were then reacted withan alkyl halide in acetonitrile at 100 C for 12-18 h. The quaternary ammonium salts 3 were precipitatedwith diethyl ether, and collected.

The synthetic route of 31241-19-7 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Levitz, Andrew; Marmarchi, Fahad; Henary, Maged; Molecules; vol. 23; 2; (2018);,
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.938465-52-2,1-Chloro-5H-pyrido[4,3-b]indole-4-carboxamide,as a common compound, the synthetic route is as follows.

To a solution of 4-(4-fluorophenyl)- 1 -oxa-4, 8-diazaspiro[5. Sjundecan-5-one (120 mg, 0.45 mmol) in NMP (3 mL) was added 1-chloro-5H-pyrido[4,3-bjindole-4-carboxamide (123 mg, 0.Smmol) and DIEA (174 mg, 1.35 mmol), and the mixture was heated under microwave irradiation for 1.5 h at 150 C.The mixture was purified with prep-HPLC to give 1-(4-(4-fluorophenyl)-5 -oxo- 1 -oxa-4, 8-diazaspiro[5.5j undecan-8-yl)-5H-pyrido [4,3-bj indole-4- carboxamide. ?H NMR (400 MHz, CD3OD) 3 8.51 (s, 1H), 8.03 (d, J=8.0 Hz, 1H), 7.82 (d, J=8.0 Hz, 1H), 7.62 (t, J=7.7 Hz, 1H), 7.54 – 7.44 (m, 1H), 7.31 – 7.23 (m, 2H), 7.14 – 7.06 (m, 2H), 4.40 (d, J=13.3 Hz, 1H), 4.27 – 4.14 (m, 2H), 4.00 – 3.90 (m, 1H), 3.80 – 3.66 (m, 3H), 3.64- 3.52 (m, 1H), 2.54 – 2.39 (m, 1H), 2.38 – 2.22 (m, 2H), 1.94 – 1.79 (m, 1H) ppm., 938465-52-2

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

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

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

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.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

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.

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

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

6855-64-7,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6855-64-7,2-Phenyl-1H-indol-5-amine,as a common compound, the synthetic route is as follows.

Example 5 Compound 5 N-(2-phenyl-1H-indol-5-yl)acetamidine Prepared in a manner similar to that of Example 1. Yield: (63percent); Elem. anal. C16H15N3 M.W.: 249.31; theory C, 77.08; H, 6.06; N, 16.85. found C, 76.97; H, 6.29; N, 16.85. IR (KBr): 3434, 3024, 1634, 1597 cm-1; 1H-NMR (d6-DMSO) 7.8-6.3 (m, 9H); 1.8 (s, 3H).; Example 7 Compound 5 As an alternative to the method described in Example 5, this product may be prepared as reported below: N-(2-phenyl-1H-indol-5-yl)acetamidine Prepared in a manner similar to that of Example 5. Yield: 60percent; Elem. anal. C16H15N3; theory C, 77.08; H, 6.06; N, 16.85. found C, 77.17; H, 5.89; N, 16.68. IR (KBr): 3434, 3024, 1634, 1597 cm-1; 1H-NMR (d6-DMSO) 7.8-6.3 (m, 9H); 1.8 (s, 3H).

The synthetic route of 6855-64-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ROTTAPHARM SPA; US2005/197331; (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