Day: March 18, 2022

676273-39-5,676273-39-5, 3-Iodo-1-tosyl-1H-indole-5-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 3 Synthesis of 3-(4-hydroxybut-1-inyl)-1-tosyl-1H-indole-5-carbonitrile (IV) 3-iodo-1-tosyl-1H-indole-5-carbonitrile (V) (12.5 g, 28.3 mmol), PdCl2 (150 mg, 0.85 mmol), PPh3 (668 mg, 2.55 mmol) and CuI (162 mg, 0.85 mmol) are suspended in a mixture of triethylamine (65 mL) and DMF (60 mL) under inert atmosphere. The mixture is heated to the temperature of 30 C., then treated with a solution (10 mL) obtained by dissolving 3-butyn-1-ol (2.7 mL, 30.0 mmol) in DMF added by slow dripping. At the end of the addition the reaction mixture is left to stand at ambient temperature and maintained under stirring overnight. The mixture is then diluted with ethyl acetate (200 mL) and treated with a solution of 1M HCl until markedly acid. The phases are separated and the organic phase is washed sequentially with a saturated solution of NaHCO3 with the addition of a 33% solution of NH4OH, an 0.1M solution of Na2S2O3 and a saturated solution of NaCl. The organic phase is dried on Na2SO4, filtered, and concentrated at low pressure. Crude product (IV) is obtained as a solid (11 g), which is not purified but used “as is” in the subsequent reaction.A portion of the crude product is purified by flash chromatography (petroleum ether/AcOEt 50/50) to obtain chemically pure product ( IV) as a white solid. [0065] 1H-NMR (400 MHz, CDCl3), delta: 7.97 (1H, d, J=8.4 Hz); 7.89 (1H, s); 7.71-7.68 (3H, m); 7.50 (1H, d, J=8.8 Hz); 7.20 (1H, d, J=8.4 Hz); 3.78 (2H, m); 3.65 (1H, bs); 2.67 (2H, t, J=6.4 Hz); 2.29 (3H, s).

676273-39-5 3-Iodo-1-tosyl-1H-indole-5-carbonitrile 21955913, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; DIPHARMA FRANCIS S.R.L.; TADDEI, Maurizio; GIANNOTTI, Luca; ATTOLINO, Emanuele; ALLEGRINI, Pietro; US2014/275542; (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

885519-01-7, 6-Bromo-4-chloro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

885519-01-7, [00611] To a solution of 6-bromo-4-chloro-1H-indole (200mg, 0.868 mmol) in 5 mL of DMF was added NaH (45.8 lmg, 1.91mmol) at 0 C and the mixture was stirred at 0 C for 1 h. SEMC1 (0.2 mL, 0.561mmol) was added dropwise slowly at 0 C and stirred at rt for 12 h. The reaction mixture was added dropwise slowly to a cold saturated aqueous NaHC03 solution at 0 C. The mixture was extracted with EtOAc (20 mL><2), and the organic layers were washed with water, brine, dried and concentrated. The crude was purified by SGC ( PE/EtOAc=100: l) to give 6-bromo-4-chloro-1H-indole (260mg, 83%) as a yellow oil. MS (EI+, m/z): 361 [M]+. 885519-01-7 6-Bromo-4-chloro-1H-indole 24728099, aindole-building-block compound, is more and more widely used in various fields. Reference：
Patent; NAVITOR PHARMACEUTICALS, INC.; MAHONEY, Sarah; MOLZ, Lisa; NARAYAN, Sridhar; SAIAH, Eddine; (516 pag.)WO2018/191146; (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.1008-07-7,7-Chloro-1H-indole-3-carbaldehyde,as a common compound, the synthetic route is as follows.,1008-07-7

General procedure: To the solution of compounds 18a-i (1 equiv) in MeCN wasadded NaH (3 equiv) and 4-Chlorobenzyl chloride (1.5 equiv) atroom temperature. The reaction mixture was stirred at roomtemperature for 4 h. The mixture was extracted with ethyl acetate,washed with brine, dried (Na2SO4), and filtered. The filtrate wasconcentrated in vacuo, and the residue was purified by columnchromatography (silica gel, ethyl acetate/Petroleum ether) to givethe desired product.

The synthetic route of 1008-07-7 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Liu, Hong-Min; Suo, Feng-Zhi; Li, Xiao-Bo; You, Ying-Hua; Lv, Chun-Tao; Zheng, Chen-Xing; Zhang, Guo-Chen; Liu, Yue-Jiao; Kang, Wen-Ting; Zheng, Yi-Chao; Xu, Hai-Wei; European Journal of Medicinal Chemistry; vol. 175; (2019); p. 357 – 372;,
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.104291-83-0,Methyl 6-cyano-1H-indole-2-carboxylate,as a common compound, the synthetic route is as follows.

Methyl 6-cyano-1H-indole-2-carboxylate (467 mg, 2.33 mmol) was dissolved in N,N-dimethylformamide (25 mL) and cooled in an ice bath. NaH (60%, 112 mg, 2.80 mmol) was added and the reaction mixture was stirred for 10 min. 2-(Chloromethyl)-1,3,5-trimethyl-benzene (472 mg, 2.80 mmol) was added and the reaction mixture was allowed to warm to room temperature and was stirred for 12 h. The reaction mixture was poured into ice water and was made acidic with the addition of 1 N HCl. The resulting precipitate was collected to give methyl 6-cyano-1-(2,4,6-trimethylbenzyl)-1H-indole-2-carboxylate. ESI-MS m/z calc. 332.2. found 333.2 (M+1)+. Retention time: 0.81 min (1 min run)., 104291-83-0

The synthetic route of 104291-83-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; VERTEX PHARMACEUTICALS INCORPORATED; Miller, Mark Thomas; Anderson, Corey; Arumugam, Vijayalaksmi; Bear, Brian Richard; Binch, Hayley Marie; Clemens, Jeremy J.; Cleveland, Thomas; Conroy, Erica; Coon, Timothy Richard; Frieman, Bryan A.; Grootenhuis, Peter Diederik Jan; Gross, Raymond Stanley; Hadida-Ruah, Sara Sabina; Haripada, Khatuya; Joshi, Pramod Virupax; Krenitsky, Paul John; Lin, Chun-Chieh; Marelius, Gulin Erdgogan; Melillo, Vito; McCartney, Jason; Nicholls, Georgia McGaughey; Pierre, Fabrice Jean Denis; Silina, Alina; Termin, Andreas P.; Uy, Johnny; Zhou, Jinglan; (590 pag.)US2016/95858; (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

118414-82-7, MK-886 is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a mixture of 3-[3-rert-butylsulfanyl-1-(4-chloro-benzyl)-5-isopropyl- lH-indol-2-yl]-2,2-dimethyl- propionic acid (1.26 mmol) and 6-bromohexyl nitrate (F. Conrad Engelhardt et a, J. Org. Chem., 2006, 71, 480-491; 1.4 mmol) in DMF (5 ml) was added CsCO3 (6 mmol). The mixture was stirred at room temperature over night. H2O was added and the reaction mixture was extracted with ethyl acetate. The extracts were washed with brine, dried over Na2SO4, filtered, and the solvent was evaporated under reduced pressure. The residue obtained was purified by silica gel chromatography (25% EtOAc in hexanes) to give the desired product.[0400] 1H NMR delta 7.63 (s, IH), 7.19 (d, 2H), 7.02 (s, 2H), 6.74 (d, 2H), 5.32 (s, 2H), 4.38 (t, 2H), 3.97 (t, 2H),3.25 (s, 2H), 3.01 (m, IH), 1.62-1.15 (m, 29H)., 118414-82-7

The synthetic route of 118414-82-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; AMIRA PHARMACEUTICALS, INC.; WO2008/67566; (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

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, (b) Step 2 A solution of tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.056 g, 0.016 mmol) in methanol (2.0 mL) was added with 4-hydroxy-1H-indole-3-carboxaldehyde (0.026 g, 0.016 mmol). Then, the mixture was added with 5 drops of piperidine, and then the mixture was stirred at 60C for 2 hours. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10)) to obtain tert-butyl (Z)-4-({6-hydroxy-2-[(4-hydroxy-1H-indol-3-yl)methylene]-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.050 g, 64%). 1H NMR (300 MHz, DMSO-d6) delta 1.38 (s, 9H), 2.53 (m, 4H), 3.38 (m, 4H), 3.88 (s, 2H), 6.55 (d, J = 7.3 Hz, 1H), 6.72 (d, J = 8.1 Hz, 1H), 6.91-7.04 (m, 2H), 7.52 (d, J = 8.1 Hz, 1H), 7.69 (s, 1H), 8.06 (d, J = 2.9 Hz, 1H), 11.87 (s, 1H).

As the paragraph descriping shows that 81779-27-3 is playing an increasingly important role.

Reference：
Patent; The University of Tokyo; Riken; NAGANO Tetsuo; OKABE Takayoshi; KOJIMA Hirotatsu; SAITO Nae; NAKANO Hirofumi; ABE Masanao; TANAKA Akiko; HONMA Teruki; YOKOYAMA Shigeyuki; TSUGANEZAWA Keiko; YUKI Hitomi; EP2565192; (2013); 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

5192-03-0, 1H-Indol-5-amine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of intermediate 16 (156?mg, 1.182?mmol, 1.0 equiv) and triethylamine (591?muL, 429?mg, 4.240?mmol, 3.6 equiv) in DCM (10?mL), acetyl chloride (101?muL, 111?mg, 1.418?mmol, 1.2 equiv) was added. The reaction was stirred at room temperature for 3?h. The mixture was poured into water and extracted with dichloromethane 3 times. The combined organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated in vacuo. Purification by flash silica gel column chromatography (7:3 hexane/ethyl acetate) afforded intermediate 7g as a clear oil (177?mg, 1.016?mmol). Yield: 85%. 1H NMR (400?MHz, CDCl3) delta 8.27 (bs, 1H), 7.80 (s, 1H), 7.30 (d, J?=?8.5?Hz, 2H), 7.20 (dd, J?=?8.8, 2.0?Hz, 2H), 6.50 (s, 1H), 2.18 (s, 3H).

5192-03-0, 5192-03-0 1H-Indol-5-amine 78867, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; See, Cheng Shang; Kitagawa, Mayumi; Liao, Pei-Ju; Lee, Kyung Hee; Wong, Jasmine; Lee, Sang Hyun; Dymock, Brian W.; European Journal of Medicinal Chemistry; vol. 156; (2018); p. 344 – 367;,
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

400071-95-6, 5-Bromo-1-methyl-1H-indole-3-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,400071-95-6

In a dry flask under argon, the carboxylic acid (2m) (100 mg, 0.39 mmol) was dissolved in dry dichloromethane (3 mL) and few drops of dry DMF. The sluggish solution was cooled to 0 C and freshly distilled oxalyl chloride (60 mg, 0.47 mmol) was added dropwise. The mixture was then stirred for 4 hours at room temperature and directly evaporated with toluene under reduced pressure. The desired acid chloride was obtained as a yellow solid and used straightaway.

400071-95-6 5-Bromo-1-methyl-1H-indole-3-carboxylic acid 11032413, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; UNIVERSITE JOSEPH FOURIER; DENIS, Jean-Noel; JOLIVALT, Claude, Marcelle; MAURIN, Max, Maurin, Louis; JEANTY, Matthieu; WO2013/14102; (2013); 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.2795-41-7,6-Fluoroindole-3-carboxaldehyde,as a common compound, the synthetic route is as follows.

General procedure: To a solution of an appropriate indole, azaindole or alternative heterocycles (1.0 eq) and di-ferf-butyl dicarbonate (1eq. to 2 eq., more in particular 1.2 eq) in acetonitrile was added DMAP (0.1 to 0.5 eq. more in particular 0.1 eq). The reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with a saturated sodium bicarbonate solution. The phases were separated. The aqueous phase was extracted with dichloromethane. The organic phases were combined, washed with a saturated ammonium chloride solution, water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The BOC-protected compound was used in the next step without further purification.

2795-41-7, As the paragraph descriping shows that 2795-41-7 is playing an increasingly important role.

Reference：
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee; CARLENS, Gunter; DALLMEIER, Kai; KAPTEIN, Suzanne; McNAUGHTON, Michael; MARCHAND, Arnaud; NEYTS, Johan; SMETS, Wim; WO2013/45516; (2013); 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.

To a solution of 4-bromo-1H-indole-7-carbonitrile (3 g, 13.57 mmol, Sinova) in EtOH (36.2 mL)/DMSO (9.05 mL) was slowly added added hydrogen peroxide (28.0 mL, 274 mmol) and NaOH (28.0 mL, 28.0 mmol). The reaction mixture was stirred at rt for about 1 h. Water was added and the precipitate was collected by filtration, washed with water, and dried under vacuum to provide 4- bromo-]H-indole-7-carboxamide (2.85 g, 88%). LC/MS (Table 1, Method R = 1.42 mm; MS m/z:280 (M+MeCN)., 1167055-46-0

The synthetic route of 1167055-46-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ABBVIE INC.; BONAFOUX, Dominique; DAVIS, Heather, M.; FRANK, Kristine, E.; FRIEDMAN, Michael, M.; HEROLD, J., Martin; HOEMANN, Michael, Z.; HUNTLEY, Raymond; OSUMA, Augustine; SHEPPARD, George; SOMAL, Gagandeep, K.; VAN CAMP, Jennifer; VAN EPPS, Stacy, A.; VASUDEVAN, Anil; WALLACE, Grier, A.; WANG, Lu; WANG, Zhi; WILSON, Noel, S.; XU, Xiangdong; WO2014/210255; (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