反応 #609296

反応方程式

ethyl 5-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylate

2-(5,6-dichloropyridin-2-yl)acetonitrile

Na2CO3

→

title compound

収率 51.6%

Ethyl 5-(2-chloro-5-(3-chloro-6-(cyanomethyl)pyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylate

収率 51.6%

溶媒

dioxane

反応条件

後処理

1. 1
   その他The reaction was further degassed
2. 2
   workup.ADDITIONFurther water (1 mL) was added
3. 3
   温度heating
4. 4
   温度before cooling to room temperature
5. 5
   ろ過The reaction was filtered through Celite
6. 6
   洗浄washing through with EtOAc
7. 7
   濃縮concentrated in vacuo
8. 8
   その他The residue was purified
9. 9
   洗浄eluting with 0-100% MeCN in water with 0.1% formic acid

実験手順

To a degassed solution of ethyl 5-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylate (Preparation 5, 1.01 g, 1.34 mmol) and 2-(5,6-dichloropyridin-2-yl)acetonitrile (Preparation 59, 300 mg, 1.60 mmol) in dioxane (10 mL) was added Na2CO3 (213 mg, 2.01 mmol), water (1 drop) and Pd(PPh3)4 (144 mg, 0.134 mmol). The reaction was further degassed and heated to 80° C. for 1 hour. Further water (1 mL) was added and heating continued for 5 hours before cooling to room temperature. The reaction was filtered through Celite washing through with EtOAc, and concentrated in vacuo. The residue was purified using reverse phase column chromatography eluting with 0-100% MeCN in water with 0.1% formic acid to afford the title compound (360 mg, 49%).

出典