反应详情

温度

110 °C

1-(Cyclohex-2-en-1-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (436 mg, 1.59 mmol), sodium carbonate (337 mg, 3.18 mmol), and 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (130 mg, 0.159 mmol) were added to a solution of N-(3-bromo-5-methylphenyl)-4-(difluoromethyl)pyrimidin-2-amine (500 mg, 1.59 mmol) in dioxane (7.5 mL). The mixture was purged with nitrogen for 5 minutes and stirred at 110° C. for 18 h. The mixture was allowed to cool to room temperature, diluted with water (30 mL) and extracted with ethyl acetate (3×50 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-50% EtOAc/hexane) to afford N-(3-(1-(cyclohex-2-en-1-yl)-1H-pyrazol-4-yl)-5-methylphenyl)-4-(difluoromethyl)pyrimidin-2-amine ESI calc'd. for C21H22F2N5 [M+H]+ 382. found 382.

1. customThe mixture was purged with nitrogen for 5 minutes
2. temperatureto cool to room temperature
3. additiondiluted with water (30 mL)
4. extractionextracted with ethyl acetate (3×50 mL)
5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by column chromatography on silica gel (0-50% EtOAc/hexane)