Potassium Carbonate → 4-{5-Cyano-7-[(1Z)-1-methylprop-1-en-1-yl]-1,3-benzoxazol-2-yl}-N-({1-[4-(trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl}methyl)benzamide

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A mixture of 4-(7-bromo-5-cyano-1,3-benzoxazol-2-yl)-N-({1-[4-(trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl}methyl)benzamide (30 mg, 0.051 mmol), [(1E)-1-methylprop-1-en-1-yl]boronic acid (18 mg, 0.18 mmol), potassium carbonate (3M solution in water) (150 μl), and 1,1′-bis(di-t-butylphosphino)-ferrocene palladium chloride (2 mg, 0.0031 mmol) in tetrahydrofuran (5 ml) was heated at reflux overnight. The mixture was diluted with ethyl acetate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography to afford the title compound. Mass spectrum (ESI) 561.2 (M+1).

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