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;,
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