Water → N-[3-(6-methoxypyridin-3-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine

참여 물질

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반응 단계

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.

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