反应 #2487461

ord-697dc41a9f784255918f1570518625e9

反应方程式

COC(=O)c1cccc(Cn2c(-c3ccsc3)cc3cc(OC)c(F)cc32)n1
methyl 6-[6-fluoro-5-methoxy-2-(thiophen-3-yl)indol-1-ylmethyl]pyridine-2-carboxylate
N
ammonia
COc1cc2cc(-c3ccsc3)n(Cc3cccc(C(N)=O)n3)c2cc1F
title compound
COc1cc2cc(-c3ccsc3)n(Cc3cccc(C(N)=O)n3)c2cc1F
6-[6-Fluoro-5-methoxy-2-(thiophen-3-yl)indol-1-ylmethyl]pyridine-2-carboxamide

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    workup.STIRRINGby stirring for 66 more hours
  2. 2
    浓缩The reaction mixture was then concentrated under reduced pressure

实验过程

A mixture of methyl 6-[6-fluoro-5-methoxy-2-(thiophen-3-yl)indol-1-ylmethyl]pyridine-2-carboxylate (168 mg) and ammonia (about 7 mol/L methanol solution, 4.2 mL) was stirred at room temperature for 6 hours. The reaction mixture was diluted with tetrahydrofuran (4.2 mL), followed by stirring for 66 more hours. The reaction mixture was then concentrated under reduced pressure to obtain the title compound (166 mg). 1H-NMR (CDCl3) δ ppm: 3.94 (3H, s), 5.45 (2H, s), 5.51 (1H, br s), 6.61 (1H, d, J=0.4 Hz), 6.90-7.00 (2H, m). 7.15 (1H, dd, J=1.3, 5.0 Hz), 7.18 (1H, d, J=8.3 Hz), 7.24 (1H, dd, J=1.3, 2.9 Hz), 7.39 (1H, dd, J=2.9, 5.0 Hz), 7.65 (1H, br s), 7.75 (1H, t. J=7.8 Hz), 8.09 (1H, d, J=7.8 Hz).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08796247B2uspto-grants-2014_08