反応 #657323

反応方程式

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

収率 17.0%

溶媒

1,4-dioxan

反応条件

後処理

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

実験手順

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.

出典