反应 #164263

反应方程式

2-(5-Bromo-2-fluoro-phenyl)-5-methyl-benzoimidazole-1-carboxylic acid tert-butyl ester

piperidine-4-carboxylic acid ethyl ester

cesium carbonate

BINAP

→

title compound

收率 99.5%

2-[5-(4-Ethoxycarbonyl-piperidin-1-yl)-2-fluoro-phenyl]-5-methyl-benzoimidazole-1-carboxylic acid tert-butyl ester

收率 99.5%

溶剂

water

toluene

toluene

反应条件

后处理

1. 1
   workup.ADDITIONthe mixture was added to the first schlenk
2. 2
   过滤the organic layer was filtered over Na2SO4
3. 3
   其他purified by flash chromatography (eluent: cyclohexane:EtOAc 8:2)

实验过程

Method 8—Step a 2-(5-Bromo-2-fluoro-phenyl)-5-methyl-benzoimidazole-1-carboxylic acid tert-butyl ester (obtained as described in general method 6, step c) (0.94 g, 2.40 mmol), piperidine-4-carboxylic acid ethyl ester (0.48 g, 3.12 mmol) and cesium carbonate (3.90 g, 12.01 mmol) were placed into a dried schlenk tube and 3 cycles of vacuum/nitrogen were performed, then dry toluene (4 mL) was added. At the same time palladium(II)acetate (0.82 g, 0.36 mmol), and BINAP (0.45 g, 0.72 mmol) were placed into a dried schlenk tube under nitrogen and 3 cycles of vacuum/nitrogen were performed. Then dry toluene (2 mL) was added, at room temperature under nitrogen, and the mixture was added to the first schlenk. The reaction mixture was heated at 80° C. overnight, water (5 mL) was added, the organic layer was filtered over Na2SO4 and then purified by flash chromatography (eluent: cyclohexane:EtOAc 8:2) to obtain 1.15 g of the title compound in quantitative yield.

来源