Month: March 2022

7506-66-3,7506-66-3, cis-Hexahydro-1H-isoindole-1,3(2H)-dione is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Under a nitrogen atmosphere, the temperature was controlled at 20 to 30 C. 300 mL of a three-necked flask was successively added with 300 mL of tetrahydrofuran and 24.0 g of zinc chloride. After 1 hour, 8.2 g of potassium borohydride was added, and stirring was continued for 1 hour. Then, 7.8 g of cis-hexahydrophthalimide was added, and the reaction was stirred for two hours. 2. OmL of concentrated sulfuric acid was added, the temperature was slowly raised, and the mixture was heated to reflux for two hours. 400 mL of toluene was added, and the mixture was distilled to an internal temperature of about 94 C, and refluxed for 3 hours. The distillation was continued at a temperature, and a portion of tetrahydrofuran was distilled off to an internal temperature of about 105 C to stop the distillation. After cooling to 30 C or less, 100 mL of 15% by mass hydrochloric acid was slowly added dropwise, and after the completion of the dropwise addition, the mixture was heated to distill off, and a part of the solvent was distilled off until the internal temperature reached about 107 C to stop. After cooling to below 30 C, 150 mL of 30% by mass sodium hydroxide was added dropwise to adjust the pH to 13-14. The steam was distilled, and the distillate was collected. The distillate was extracted with 3×100 mL of dichloromethane, and then dried over anhydrous sodium sulfate. The desiccant was filtered off, and the solvent was evaporated under reduced pressure to give 6.0 g of pale yellow transparent liquid,cis-perhydroisoindole

7506-66-3 cis-Hexahydro-1H-isoindole-1,3(2H)-dione 6992236, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Jiangxi Jimin Trustworthy Pharmaceutical Co., Ltd.; Jiangxi Jimin Trustworthy Group Co., Ltd.; Guo Linfeng; Wen Wanjiang; Peng Changchun; Zhang Keqin; He Pingqing; Li Yibao; (6 pag.)CN108752260; (2018); A;,
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

434958-85-7,434958-85-7, N-Boc-5-Hydroxyindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of compound III-2 (3.2 g, 13.7 mmol)Was dissolved in 20 mL of CH2Cl2,Diisopropylethylamine (1.77 g, 13.7 mmol)Was dissolved in 120 mL of tetrahydrofuran,Mixed with both,The mixed solution was then slowly added to triphosgene (1.3 g, 4.38 mmol)In CH2Cl2 (100 mL)After stirring at room temperature for 1 h,A mixture of 1,4-diazabicyclo [3.2.2] nonane (1.72 g, 13.7 mmol)Of the CH2Cl2 solution was slowly added thereto,Reaction at room temperature for 4 h;After completion of the reaction, add H2O dilution withCHCl3, the organic phase was collected, washed with saturated aqueous NaCl solution, dried over anhydrous Na2SO4, the solvent was removed to give the crude product;CHCl3 and CH3OH (90:10) as the developing solvent. The product III-3 (2.4 g, 45%) was isolated.

434958-85-7 N-Boc-5-Hydroxyindole 22596220, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Beijing Normal University; Zhang Huabei; Wang Huan; Fang Yu; Liu Jianping; Wang Shuxia; (32 pag.)CN107188900; (2017); A;,
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.118959-44-7,1-Methyl-1H-indole-3-carboxamide,as a common compound, the synthetic route is as follows.

General procedure: Lawesson?s reagent (0.38 g, 0.96 mmol for compound 7f or 0.80 g, 2 mmol for compounds 8a-f and 9a-e) was added to a solution of appropriate derivatives 7f (0.17 g, 0.95 mmol) or 8a-f and 9a-e (4 mmol) in anhydrous toluene or benzene (20 mL). The mixture was heated at reflux under nitrogen atmosphere for 0.5-24 h. After cooling the solvent was evaporated under reduced pressure and the residue was purified by column chromatography using ethyl acetate (for compound 10f), dichloromethane /ethyl acetate (98/2) (for compounds 11a-f) or dichloromethane (for compounds 12a-e) as eluent. For compounds 10f, 11a-f and 12a,c-e see supplementary material., 118959-44-7

118959-44-7 1-Methyl-1H-indole-3-carboxamide 823187, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Carbone; Pennati; Barraja; Montalbano; Parrino; Spano; Lopergolo; Sbarra; Doldi; Zaffaroni; Cirrincione; Diana; Current Medicinal Chemistry; vol. 21; 14; (2014); p. 1654 – 1666;,
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.227960-12-5,Methyl 5-methylindole-3-carboxylate,as a common compound, the synthetic route is as follows.

1.63 g (11.8 [MMOL)] of potassium carbonate are added at [25C] under an argon atmosphere to 0.895 g (4.73 [MMOL)] of [3-METHOXYCARBONYL-5-METHYL-1 H-INDOLE] in 10 cm3 of dimethyl sulphoxide. After stirring at [25C] for 0.5 hour, 0.774 g (4.73 [MMOL)] of 2-chloroquinoline is added. After stirring at [100C] for 48 hours, the reaction mixture is cooled and diluted with 100 cm3 ethyl acetate and then washed with 3 times 50 cm3 of water and 25 cm3 of saturated aqueous sodium chloride solution. After separating the phases by settling, the organic phase is dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 1.2 g of a residue which is recrystallised under hot conditions from 30 cm3 of cyclohexane and 6 cm3 of ethyl acetate to give 0. 8 g of [3-METHOXYCARBONYL-5-METHYL-] [1-(QUINOL-2-YL)-1 H-INDOLE] in the form of a white solid melting at [143C.], 227960-12-5

227960-12-5 Methyl 5-methylindole-3-carboxylate 2759866, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; AVENTIS PHARMA DEUTSCHLAND GMBH; WO2004/7480; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.101861-63-6,4,6-Dichloroindole-2-carboxylic acid,as a common compound, the synthetic route is as follows.

In the reaction bottle,22 g of 4,6-dichloroindolecarboxylic acid was added to 150 mL of DMSO, and then 3 g of copper chloride was added.The reaction was heated at 120 C for 1 h,TLC monitors the reaction of the starting material completely, and the reaction solution is filtered, and then 200 mL of dichloromethane is added to extract the reaction solution three times.The organic phases were combined, washed with 200 mL of water and concentrated.Then in a mixture of acetone and n-hexane (V acetone: V-hexane = 3:1)Recrystallization from 100 mL gives 4,6-dichloroanthracene 14g, 101861-63-6

101861-63-6 4,6-Dichloroindole-2-carboxylic acid 127988, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Henan Normal University; Xu Guiqing; Wang Jiahao; Ren Baoqi; Zhou Yingjie; Mao Longfei; (9 pag.)CN109160895; (2019); A;,
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,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 1,4,8-triazaspiro[5.Sjundecan-5-one (30 mg, 0.l8mmol) inNMPmL) was added 1-chloro-5H-pyrido[4,3-bjindole-4-carboxamide (44 mg, 0.l8mmol) andDIEA (70 mg, 0.S4mmol), and the mixture was heated under microwave irradiation for 1.5 h at150 C. The reaction solution was purified by prep-HPLC to afford 1-(5-oxo-1,4,8-triazaspiro[5 . Sjundecan-8-yl)-5H-pyrido[4,3-bjindole-4-carboxamide. MS: 379.3 [M+Hjt 1HNMR (400 MHz, DMSO-d6) 3 11.93 (s, 1H), 9.67 (br. s., 1H), 8.70 (s, 1H), 8.54 (br. s., 1H),8.19 (br. s., 1H), 8.05 (d, J=7.8 Hz, 1H), 7.83 (d, J=8.0 Hz, 1H), 7.54 (br. s., 1H), 7.48 (t, J7.4Hz, 1H), 7.38 – 7.31 (m, 1H), 4.39 (d, J=14.1 Hz, 1H), 3.93 (d, J=12.5 Hz, 2H), 3.56 – 3.49 (m,2H), 3.45 (br. s., 2H), 2.98 (t, J=11.5 Hz, 1H), 2.40 -2.21 (m, 2H), 2.20 – 2.05 (m, 1H), 1.84 (d,J13.1 Hz, 1H) ppm.

938465-52-2 1-Chloro-5H-pyrido[4,3-b]indole-4-carboxamide 59198457, aindole-building-block compound, is more and more widely used in various fields.

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

162100-95-0, 6-Fluoro-5-methyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Synthesis of intermediate 8a: Diethylaluminum chloride 1 M in hexane (17.0 mL, 17.0 mmol) was added dropwise, at 0C and under N2-atmosphere, to a solution of 6-fluoro-5-methyl- 1 H-indole [CAS 162100-95-0] (1 .69 g, 1 1 .3 mmol) in CH2CI2 (150 mL). After 15 min at 0C, a solution of 2-(2-(2-(benzyloxy)ethoxy)-4-chlorophenyl)acetyl chloride 1e (5.37 g, 15.8 mmol, synthesis: see Example 1 ) in CH2CI2 (100 mL) was slowly added. The reaction mixture was stirred at 0C for 1 h and at room temperature for 2 h. The reaction mixture was poured out into an ice/Rochelle salt solution and the mixture was vigorously stirred. The layers were separated. The organic layer was dried over MgSO4 and filtered over a short pad of dicalite. The filter cake was rinsed a few times with THF and the combined filtrates were concentrated under reduced pressure. The solid residue was suspended in CH3CN (20 mL), filtered off, washed with a small amount of CH3CN, and dried under vacuum at 50 C to give 2-(2-(2-(benzyloxy)ethoxy)-4- chlorophenyl)-1 -(6-fluoro-5-methyl-1 H-indol-3-yl)ethanone 8a (2.39 g) as a white solid., 162100-95-0

As the paragraph descriping shows that 162100-95-0 is playing an increasingly important role.

Reference：
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; KESTELEYN, Bart Rudolf Romanie; RABOISSON, Pierre Jean-Marie Bernard; BONFANTI, Jean-Francois; JONCKERS, Tim Hugo Maria; BARDIOT, Dorothee Alice Marie-Eve; MARCHAND, Arnaud Didier M; (75 pag.)WO2017/46255; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.525593-33-3,3-Bromo-5-nitroindole,as a common compound, the synthetic route is as follows.

To a stirred solution of 3-bromo-5-nitro-lH-indole (2) (100.0 g, 0.414 mol) in DMF (1 L) was added NaH (19.9 g, 0.829 mol) at 0 C and the solution was stirred for 0.5 h. Methyl iodide (87.7 g, 0.622 mol) was then added to the reaction mixture and the solution was stirred at RT for another 2 h. After completion of reaction the mixture was quenched with water and extracted with ethyl acetate. The organic extract was dried over anhydrous sodium sulphate, filtered and solvents evaporated from the filtrate under reduced pressure to obtain a crude, which was purified by column chromatography on silica gel (100-200 mesh), eluted with 10-15% gradient of EtOAc in pet-ether, to afford 3 -bromo-l -methyl-5 -nitro-lH- indole (101.0 g, 95%)., 525593-33-3

Big data shows that 525593-33-3 is playing an increasingly important role.

Reference：
Patent; COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH; SRIVARI, Chandrasekhar; MAINKAR, Prathama Satyendra; REDDY, Chada Raji; KOTAMRAJU, Srigiridhar; TOGAPUR, Pavan Kumar; MUPPIDI, Subbarao Mohan Venkata; SHARMA, Somesh; JHA, Ashok Kumar; ARUMUGAM, Prem Kumar; (27 pag.)WO2019/102488; (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

393553-57-6, 6-Bromo-4-methoxy-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

393553-57-6, To a solution of 6-bromo-4-methoxy-lH-indole A.85 (2.0 g, 8.85 mmol) in DMF (9 mL) was added (chloromethylene)dimethylamrnonium chloride (1.699 g, 13.27 mmol) and the mixture was stirred at room temperature for 24 hours. To the mixture was added water (50 mL) and 10 N aqueous NaOH (10 mL) and the mixture was heated at reflux for 1 hour. The mixture was cooled to 0 0C. The resulting precipitate was collected by filtration to give 6-bromo-4- methoxy-lH-indole-3-carbaldehyde A.140 (1.392 g, 61.9% yield) as a brown solid: 1H NMR (400 MHz, DMS0-d6) delta ppm 12.26 (1 H, s), 10.26 (1 H, s), 8.05 (1 H, s), 7.30 (1 H, d, J=I .5 Hz), 6.89 (1 H, d, J=I .1 Hz), 3.95 (3 H, s); Mass Spectrum (ESI) m/e = 253.9 [M+l (79Br)] and 255.9 [M+l (81Br)].

As the paragraph descriping shows that 393553-57-6 is playing an increasingly important role.

Reference：
Patent; AMGEN INC.; WO2009/158011; (2009); 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

434958-85-7,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.434958-85-7,N-Boc-5-Hydroxyindole,as a common compound, the synthetic route is as follows.

Example 93C; 5 -[4-(4-Bromo-phenylcarbamoyl)-2-nitro-phenoxy]-indole- 1-carboxylic acid tert-butyl ester; [0465] The products of Example 1OA (406.5 mg, 1.145 mmol) and Example 93B (267 mg, 1.145 mmol) were dissolved in anhydrous N,N-dimethylformamide (8 mL), treated with potassium carbonate (316 mg, 2.289 mmol), and heated at 80 under a nitrogen atmosphere for 3 hours. The reaction was cooled to room temperature and the solvent removed by rotary evaporation under vacuum. The residue was taken up in water (50 mL) and extracted with ethyl acetate (2 x 50 mL). The combined organic extracts were washed with brine (25 mL), dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation under vacuum. Purification by silica gel flash chromatography using 1% ethyl acetate/methylene chloride as eluent provided the title compound as a yellow foam (519 mg, 82%).

As the paragraph descriping shows that 434958-85-7 is playing an increasingly important role.

Reference：
Patent; ABBOTT LABORATORIES; WO2007/76034; (2007); A2;,
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