Day: March 9, 2022

90924-06-4, 1-Methyl-4-indolecarboxylic Acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,90924-06-4

To a solution of 4-METHYL-4- [ (3S)-3-METHYL-4- [ (1 R)-1- [4- (TRIFLUOROMETHYL) PHENYL] ETHYL] PIPERAZIN-1-YL]-1-PIPERIDINECARBOXYLIC ACID-DIMETHYLETHYL ester (127 mg, 0.27 MMOL) in CH2CI2 (3 mL) was added trifluoromethyl acetic acid (1.5 mL) at room temperature. After 2h the reaction mixture was concentrated in vacuo, and dried under vacuum for 3 h. Re-dissolved the product in DMF (5 mL), then 1-methyl-1 H-indol-4-carboxylic acid (52 mg, 0.30 MMOL), Et3N (55 mg, 0.54 MMOL), and HATU (134 mg, 0.35 MMOL) was added successively at room temperature. After 16 h the reaction mixture was poured into ice water (10 mL), and the mixture was extracted with EtOAc (3X20 mL). The organic phase was washed with NAHCO3 (10 mL, sat. ) and brine (10 mL), and dried over NA2SO4. Concentration in vacuo, and purification by column chromatography (CH2CI2-MEOH, 9: 1) afforded the title compound as a yellow solid. MS: 526 (M+).’H NMR (CDCl3, 400MHZ) : S : 0.9 (s, 3H), 1.14 (d, 3H), 1.3 (d, 4H), 1.4-1. 8 (m, 2H), 1.82-2. 05 (m, 1H), 2.18-2. 8 (m, 6H), 2.9-3. 1 (m, 1H), 3.1-3. 3 (m, 1H), 3.3-3. 7 (m, 2H), 3.8 (s, 3H), 3.9-4. 3 (m, 2H), 6.48 (m, 1H), 7.05-7. 16 (m, 2H), 7. 18-7. 28 (M, 1 H), 7.3-7. 38 (m, 1 H), 7.46-7. 6 (m, 4H).

As the paragraph descriping shows that 90924-06-4 is playing an increasingly important role.

Reference：
Patent; SCHERING AKTIENGESELLSCHAFT; WO2004/113323; (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.227960-12-5,Methyl 5-methylindole-3-carboxylate,as a common compound, the synthetic route is as follows.

Methyl 5-methyl-1H-indole-3-carboxylate (200 mg, 1.06 mmol) used hydrolysis reaction (2 NNaOH water solution) to aord DX-01-03 (white solid, 150 mg, yield 81%). 1H-NMR (400 MHz,CD3OD): = 8.15 (d, J = 1.8 Hz, 1H, H-indolyl), 8.07 (s, 1H, H-indolyl), 7.39 (d, J = 8.3 Hz, 1H,H-indolyl), 7.15 (dd, J = 8.3, 1.1 Hz, 1H, H-indolyl), 2.46 (s, 3H, CH3). 13C-NMR (101 MHz, CD3OD): = 137.41, 134.35, 127.80, 127.00, 122.51, 120.09, 117.20, 113.08, 110.78, 21.77. HRMS (ESI): m/z [M + H]+calculated for C10H10NO2: 176.07061; found: 176.07094., 227960-12-5

As the paragraph descriping shows that 227960-12-5 is playing an increasingly important role.

Reference：
Article; Wen, Hui; Liu, Yuke; Wang, Shufang; Wang, Ting; Zhang, Gang; Chen, Xiaoguang; Li, Yan; Cui, Huaqing; Lai, Fangfang; Sheng, Li; Molecules; vol. 24; 11; (2019);,
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

10075-48-6, 5-Bromo-3-methyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

10075-48-6, Step B 5-Bromo-1,3-dimethylindole To a stirred solution of 5-bromo-3-methylindole (2.85 g., 13.6 mmol., 1 eq.) in DMF (35 mL.) was added NaH (651 mg. of a 60% dispersion in oil, 16.28 mmol., 1.2 eq.). The mixture was stirred 15 minutes. To this mixture was added iodomethane (0.930 mL., 14.93 mmol., 1.1 eq.). The mixture was stirred for 2 hours. The DMF was removed in vacuo. The residue was diluted with water and extracted 4* with Et2 O. The organic extracts were combined, dried over anhydrous MgSO4, filtered and concentrated in vacuo giving 3.04 g. 5-bromo-1,3-dimethylindole as a reddish liquid.

10075-48-6 5-Bromo-3-methyl-1H-indole 254707, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Merck & Co., Inc.; US5252732; (1993); 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

39689-58-2, 2-(1H-Indol-6-yl)acetic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

h. N-Cyclopentylmethylindole-6-acetamide A solution of indole-6-acetic acid (0.70 g) and 1,1′-carbonyldiimidazole (0.83 g) in methylene chloride (20 ml) and N,N-dimethylformamide (5 ml) was heated at reflux for 20 min, treated with cyclopentylmethylamine (0.59 g), and heated at reflux for an additional 3 hr. The solution was diluted with methylene chloride; washed successively with 10% v/v hydrochloric acid, water and brine; dried (MgSO4); and evaporated. The residue was purified by flash chromatography, eluding with 1:19 ethyl acetate: hexane, to give N-cyclopentylmethylindole-6-acetamide (0.83, 81%) as a white powder; partial NMR (80 MHz, CDCl3): 3.13(t, 2H, NHCH2), 3.69(s, 2H, ArCH2), 6.55(m, 1H, H3 -indole), 6.98(dd, 1H, H5 -indole), 7.62(d, 1H, H4 -indole)., 39689-58-2

As the paragraph descriping shows that 39689-58-2 is playing an increasingly important role.

Reference：
Patent; ICI Americas Inc.; US4894386; (1990); 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

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

A solution of 6-fluoro-5-methyl-1 H-indole [CAS 162100-95-0] (1.7 g, 11 .4 mmol) in CH2CI2 (100 mL) was cooled to 0C under N2-atmosphere. A solution of diethylaluminum chloride 1M in hexane (17.1 mL, 17.1 mmol) was added dropwise and the resulting mixture was kept at 0C for 15 mm. A solution of 2-(4-chloro-2-methoxyphenyl)acetyl chloride 9a? (3.50 g, 16 mmol) in CH2CI2 (50 mL) was added dropwise. Stirring was continued at 0C for 1 h and the reaction mixture was subsequently stirred at room temperature for 2 h. The reaction mixture was poured out into a stirring ice/Rochelle salt solution. After the ice had melted, the mixture was filtered over dicalite and the filter cake was washed several times with THE.The filtrates were combined. The layers were separated and the organic layer was washed with brine, dried over Mg504, filtered and evaporated under reduced pressure. The solid residue was suspended in CH2CI2 (30 mL) and the precipitate was filtered off and dried under vacuum at 500C to provide 2-(4-chloro-2- methoxyphenyl)-1 -(6-fluoro-5-methyl-1 H-indol-3-yl)ethanone 9a (2.76 g)., 162100-95-0

The synthetic route of 162100-95-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee Alice Marie-Eve; BONFANTI, Jean-Francois; COESEMANS, Erwin; KESTELEYN, Bart Rudolf Romanie; MARCHAND, Arnaud Didier M; RABOISSON, Pierre Jean-Marie Bernard; (96 pag.)WO2017/167952; (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

1265231-91-1, 3-(Dimethylamino)-2-(1-(phenylsulfonyl)-1H-indole-2-carbonyl)acrylonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

N-(5-Hydrazinyl-1H-benzo[d]imidazol-2-yl)acetamidedihydrochloride 3d (500mg, 1.8mmol) and 3-(dimethylamino)-2-(1-(phenylsulfonyl)-1H-indole-2-carbonyl)acrylonitrile 1f (477mg, 1.26mmol) were suspended in 20mL of absoluteethanol, the reaction solution was refluxed for 4 hours. The solution was subjected to suction filtration, the filtercake was washed with 5mL of ethanol then the filtrate was concentrated under reduced pressure. The residue wasfurther separated and purified by silica gel column chromatography (developing agent: system B) to obtainN-(5-(5-amino-4-(1-(phenylsulfonyl)-1H-indole-2-carbonyl)-1H-pyrazol-1-yl)-1H-benzo[d]imida zol-2-yl) acetamide 3e(134mg, brown solid), yield: 13.8%.MS m / z (ESI): 539.8 [M + 1]

1265231-91-1, The synthetic route of 1265231-91-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Zhejiang Hisun Pharmaceutical Co., Ltd; CHEN, Lei; GUAN, Dongliang; BAI, Hua; YAN, Xing; MIAO, Shuai; ZHU, Songsong; (54 pag.)EP3339305; (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.59908-47-3,5-Chloro-1-methyl-1H-indole-2-carboxylic acid,as a common compound, the synthetic route is as follows.

59908-47-3, Step 3: Synthesis of 5-chloro-l-methyl-N-{4-[(pyrimidin-2-yl)({[2- (trimethylsilyl)ethoxy] methyl})sulfamoyl]phenyl}-lH-indole-2-carboxamide 43.3 [00511] To a solution of 5-chloro-l-methyl-lH-indole-2-carboxylic acid (43.2, 81 mg, 0.39 mmol) in MeCN (dry, 5ml) was added 4-amino-N-phenyl-N-{[2- (trimethylsilyl)ethoxy]methyl}benzene-l-sulfonamide (150 mg, 0.4 mmol) and 3-picoline (57 mu, 0.58 mmol). To this solution was added methanesulfonyl chloride (36 mu, 0.46 mmol) and the mixture was stirred under nitrogen at rt. After 60h the solvent was removed in vacuo and the crude material purified by flash column chromatography (heptane/EtOAc 80/20 to 60/40) to obtain 97 mg (43%) of 5-chloro-l-methyl-N-{4-[(pyrimidin-2-yl)({[2- (trimethylsilyl)ethoxy]methyl})sulfamoyl]phenyl}-lH-indole-2-carboxamide 43.3 as a white powder.

The synthetic route of 59908-47-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; RAZE THERAPEUTICS, INC.; SAIAH, Eddine; (148 pag.)WO2016/40449; (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

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

To the mixture of Intermediate 1(1 g, 4.07 mmol) in 30 mL of CF3COOH was added NIS (0.916 g, 4.07 mmol), then the mixture was stirred at room temperature overnight.Water (200 mL) was added into the mixture after it was cooled to room temperature, which wasfiltered and washed with water to yield 1 -chloro-8-iodo-5H-pyrido[4,3 -bj indole-4-carboxamide,which was used in the next step without further purification. ?HNMR(300MHz, DMSO-d6)oe12.33 (s, 1 H), 8.67 (s, 1 H), 8.61 (s,1 H), 8.37 (s, 1 H), 7.83 (d, J=8.4 Hz, 1 H), 7.61 (d, J=8.4Hz, 1 H) ppm.

The synthetic route of 938465-52-2 has been constantly updated, and we look forward to future research findings.

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

101861-63-6, 4,6-Dichloroindole-2-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A flask was charged with tert-butyl l,8-diazaspiro[4.5]decane-8-carboxylate (165 mg, 0.69 mmol, 1 equiv), 4,6-dichloro-lH-indole-2-carboxylic acid (219 mg, 0.95 mmol, 1.39 equiv) and DMF (5 mL). The mixture was stirred until all reagents were solubilized prior to the addition of HATU (339 mg, 0.89 mmol, 1.29 equiv) and TEA (383 mu, 2.75 mmol, 3.99 equiv). The reaction mixture was stirred overnight at room temperature, poured into EtOAc (5 mL), washed with sat. NaHC03 (5 mL) and brine (5 mL), dried over Na2S04, concentrated under reduced pressure, and purified over silica to afford tert-butyl l-(4,6-dichloro-lH-indole-2- carbonyl)-l,8-diazaspiro[4.5]decane-8-carboxylate (247 mg, 79% yield). LCMS (ESI, m/z): 452.1 [M+H]+.

101861-63-6, As the paragraph descriping shows that 101861-63-6 is playing an increasingly important role.

Reference：
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; WEBER, Olivia D.; BUZARD, Daniel J.; SHAGHAFI, Michael B.; JONES, Todd K.; (275 pag.)WO2019/46318; (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

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

General procedure: Piperidine (0.08 mL) was added to methanol (25 mL) dissolved in substituted aldehydes 5-7 (0.18 mmol) and starting 2-indolinone derivatives 8-11 (0.18 mmol) which were prepared as described previously refPreviewPlaceHolder[6], refPreviewPlaceHolder[21], refPreviewPlaceHolder[22], refPreviewPlaceHolder[23], refPreviewPlaceHolder[24] and refPreviewPlaceHolder[25]. The mixture was refluxed for 5 h. For the targeted compounds 12-21 and 28-36, the mixture was evaporated to remove the solvent and the residue was purified by column chromatography (CH2Cl2/MeOH 100:1-10:1). For the targeted compounds 22-27, ethyl ether (15 mL) was added to the residue and the yellow precipitate was collected by filtration. The obtained precipitate was subjected to the hydrogen chloride saturated methanol to afford it as hydrochloride derivative. All the targeted compounds 12-36 show moderate to good yields under this reaction condition with the yields of 60-92%.

2795-41-7, The synthetic route of 2795-41-7 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Zou, Hongbin; Zhang, Liang; Ouyang, Jingfeng; Giulianotti, Marc A.; Yu, Yongping; European Journal of Medicinal Chemistry; vol. 46; 12; (2011); p. 5970 – 5977;,
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