Category: 129822-45-3

129822-45-3, tert-Butyl 4-fluoro-1H-indole-1-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of diisopropylamine (175 mL, 1.25 mol) in THF (800 mL) at 0 Cwas added n-BuLi (500 mL, 1.25 mol, 2.5 Min hexane) dropwise. The mixture was stirred at 0C for 40 min. Then the mixture was cooled to -78 C. Tert-butyl 4-fluoro-1H-indole-1-carboxylate (118 g, 0.50 mol) in THF (300 mL) was added dropwise slowly, followed by5 triisopropyl borate (231 mL, 1. 00 mol). The mixture was stirred at -78 C for another 40 min.The reaction was monitored by HPLC. When the reaction was completed, the reaction wasquenched with NH4Cl (sat. 500 mL). Then the mixture was adjusted to pH= 6 with 1 N HCl.Extracted with EtOAc (2000 mL) and the combined organic layers were washed with brine (500mL), dried over Na2S04, filtered and concentrated. The obtained solid was recrystallized with10 EtOAc and PE to give (1-(tert-butoxycarbonyl)-4-fluoro-1H-indol-2-yl)boronic acid (93 g, yield:64%, store in fridge). 1H-NMR (CDCh, 400 MHz) 8 7.77 (d, J = 8.4 Hz, 1H), 7.57 (s, 1H), 7.44(s, 2H), 7.24 (m, 1H), 6.90 (m, 1H), 1.66 (s, 9H). MS (M+Ht: 280.

129822-45-3, 129822-45-3 tert-Butyl 4-fluoro-1H-indole-1-carboxylate 14710388, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; BROCKUNIER, Linda L.; NARGUND, Ravi; MARCANTONIO, Karen; ZORN, Nicolas; XIAO, Dong; PENG, Xuanjia; LI, Peng; GUO, Tao; WO2014/121416; (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.129822-45-3,tert-Butyl 4-fluoro-1H-indole-1-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of diisopropylamine (175 mL, 1.25 mol) in THF (800 mL) at 0C was added n-BuLi (500 mL, 1.25 mol) dropwise. The mixture was stirred at 0C for 40 minutes. Then the mixture was cooled to -78 C. Tert-butyl4-fluoro-1H-indole-1-carboxylate (118 g, 0.50 mol) inTHF (300 mL) was added dropwise, followed by triisopropyl borate (231 mL, 1.00 mol). The mixture was stirred at -78 C for another 40 mm. The reaction was monitored by HPLC. When the reaction was completed, the reaction was quenched with NH4C1 (sat. 500 mL). Then the mixture was adjusted to pH = 6 with 1 N HC1, extracted with EtOAc (2000 mE) and the combined organic layers were washed with brine (500 mL), dried over Na2504, filtered and concentrated. Theobtained solid was recrystallized with EtOAc and PE to give (1-(tert-butoxycarbonyl)-4-fluoro-1H- indol-2-yl)boronic acid (93 g, yield: 64%). ?H-NMR (CDC13, 400 MHz) 7.77 (d, J 8.4 Hz, 1H), 7.57 (s, 1H), 7.44 (s, 2H), 7.24 (m, 1H), 6.90 (m, 1H), 1.66 (s, 9H). MS (M+H): 280.

129822-45-3, As the paragraph descriping shows that 129822-45-3 is playing an increasingly important role.

Reference£º
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