反应详情

温度

80 °C

A solution of 1-(6-bromo-4-chloro-3′,5′-difluorobiphenyl-2-yl)ethanone (300 mg, 0.87 mmol), 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (250 mg, 0.96 mmol), and sodium carbonate (280 mg, 2.6 mmol) in 1,4-dioxane (3.0 mL, 38 mmol) was degassed with nitrogen 5 minutes, treated with tetrakis(triphenylphosphine)palladium(0) (100 mg, 0.087 mmol) degassed with additional nitrogen for 5 mins, and heated at 80° C. overnight. The reaction mixture was diluted with water and extracted with ethyl acetate (2×60 mL). The combined organic layers were washed with water and brine, dried with sodium sulfate, filtered, and concentrated to a crude residue. Purification via preparative LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min) gave the desired product (190 mg, 54%).

1. customdegassed with additional nitrogen for 5 mins
2. additionThe reaction mixture was diluted with water
3. extractionextracted with ethyl acetate (2×60 mL)
4. washThe combined organic layers were washed with water and brine
5. dry with materialdried with sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated to a crude residue
8. customPurification via preparative LCMS (XBridge C18 column
9. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min)