反应详情

温度

75 °C

N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (150 mg, 0.411 mmol) and potassium fluoride (71.6 mg, 1.23 mmol) were added to 3.00 mL of a stock solution of palladium(II) acetate (4.61 mg, 0.021 mmol) and butyl[di-(3S,5S,7S)-tricyclo[3.3.1.13,7]dec-1-yl]phosphane (14.7 mg, 0.041 mmol) in THF (3.00 mL) under nitrogen. 5-Bromo-2-methoxypyridine (0.069 mL, 0.534 mmol) and water (1.00 mL) were then added to the reaction mixture and was heated to 75° C. for 17 hours. Upon cooling to room temperature, the reaction mixture was quenched by the addition of 25% aqueous NH4OAc. The aqueous layer was extracted with ethyl acetate (2×) and the combined organic layers were washed sequentially with water and brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/dichloromethane) to afford N-[3-(6-methoxypyridin-3-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine as a beige solid. MS APC calc'd for C17H14F3N4O [M+H]+ 347. found 347.

1. temperatureUpon cooling to room temperature
2. customthe reaction mixture was quenched by the addition of 25% aqueous NH4OAc
3. extractionThe aqueous layer was extracted with ethyl acetate (2×)
4. washthe combined organic layers were washed sequentially with water and brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel chromatography (ethyl acetate/dichloromethane)