反应 #657323

反应方程式

sodium carbonate

3-Bromo-2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine

N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetamide

→

N-{4-[2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl]pyridin-2-yl}acetamide

收率 17.0%

溶剂

1,4-dioxan

反应条件

后处理

1. 1
   其他The reaction mixture is flushed with argon for 5 mins
2. 2
   其他sealed
3. 3
   workup.ADDITIONThe reaction mixture is then poured in water
4. 4
   萃取extracted with dichloromethane (3×20 mL)
5. 5
   干燥The organic layer is dried over anhydrous magnesium sulphate
6. 6
   过滤filtered
7. 7
   浓缩concentrated under reduced pressure
8. 8
   其他The crude material is purified by column chromatography

实验过程

3-Bromo-2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine (150 mg, 0.51 mmol) and N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetamide (148 mg, 0.56 mmol, 1.1 eq) are dissolved in 1.5 mL 1,4-dioxan. To this mixture, bis(tricyclohexylphosphine)palladium(II)-dichloride (57 mg, 0.07 mmol, 0.15 eq) and 0.83 mL sodium carbonate solution (2 molar) are added. The reaction mixture is flushed with argon for 5 mins and then sealed. Next the mixture is heated for 30 min at 150° C. in the microwave (Biotage). The reaction mixture is then poured in water and extracted with dichloromethane (3×20 mL). The organic layer is dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure. The crude material is purified by column chromatography using silica gel in heptane and ethyl acetate (1:0 to 1:1) as eluent and 0.03 g (17%) of N-{4-[2-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-3-yl]pyridin-2-yl}acetamide are obtained as a white solid.

来源