反应 #61517

反应方程式

4-Iodo-5-thiophen-2-yl-2H-pyrazole-3-carboxylic acid ethyl ester

copper cyanide

→

4-Cyano-5-thiophen-2-yl-2H-pyrazole-3-carboxylic acid ethyl ester

溶剂

DMF

反应条件

后处理

1. 1
   其他20 ml of tetrahydrofuran and the solution was degassed with argon
2. 2
   其他The solvent was removed under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
4. 4
   洗涤this solution was washed with saturated aqueous sodium bicarbonate
5. 5
   干燥The organic phase was dried with sodium sulfate
6. 6
   过滤filtered
7. 7
   其他the solvent was removed under reduced pressure
8. 8
   其他The product was purified by silica gel chromatography
9. 9
   洗涤eluting with n-heptane

实验过程

1.57 g (4.5 mmol) of 4-Iodo-5-thiophen-2-yl-2H-pyrazole-3-carboxylic acid ethyl ester, 0.81 g (9.0 mmol) of copper cyanide and 352 mg (2.3 mmol) of tetraethylammonium cyanide were dissolved in 10 ml of DMF and 20 ml of tetrahydrofuran and the solution was degassed with argon. 223 mg (0.2 mmol) of Tris(dibenzylideneacetone)dipalladium (0) and 374 mg (0.7 mmol) of 1,1′-bis-(diphenylphosphino) ferrocene were added at RT. The reaction was stirred at 120° C. for 5 h. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and this solution was washed with saturated aqueous sodium bicarbonate. The organic phase was dried with sodium sulfate, filtered and the solvent was removed under reduced pressure. The product was purified by silica gel chromatography eluting with n-heptane:ethyl acetate/1:1.

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