反应 #45398

反应方程式

mixture

7-iodo-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-4-amine

tert-butyl acrylate

triethylamine

→

desired product

收率 61.0%

tert-butyl (2E)-3-[4-amino-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-7-yl]acrylate

收率 61.0%

溶剂

DMF

反应条件

后处理

1. 1
   温度The resulting mixture was cooled to room temperature
2. 2
   其他partitioned between water and ethyl acetate
3. 3
   萃取The organic extract
4. 4
   洗涤was washed with brine
5. 5
   干燥dried (Na2SO4)
6. 6
   过滤filtered
7. 7
   浓缩concentrated
8. 8
   其他The residue was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes

实验过程

A mixture of Example 10B (0.417 g, 0.94 mmol), tert-butyl acrylate (0.26 mL, 1.74 mol) and triethylamine (0.7 mL, 5 mmol) in DMF (3 mL) was degassed with nitrogen for 45 minutes, treated with PdCl2(o-tol3P)2 (0.032 g, 0.046 mmol), and heated to 80° C. overnight. The resulting mixture was cooled to room temperature, then partitioned between water and ethyl acetate. The organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes to provide 0.25 g (61% yield) of the desired product. MS (ESI(+)) m/e 445 (M+H)+.

来源