2-Bromo-1-(4-fluorophenyl)ethan-1-one → 4-(2-{5-[2-(4-Fluoro-phenyl)-2-oxo-ethylamino]-2-methyl-phenyl amino}-oxazol-5-yl)-benzonitrile

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Reaction Steps

To a solution of 4-[2-(5-Amino-2-methyl-phenylamino)-oxazol-5-yl]-benzonitrile (60 mg, 0.207 mmol) in dimethylacetamide (3 mL) was added 4-fluorophenacyl bromide (45 mg, 0.207 mmol), NaHCO3 (18 mg, 0.207 mmol). The mixture was stirred at room temperature for 2 h. After removal of the solvent, the residue was treated with saturated aqueous NaHCO3 (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine (20 mL), dried over MgSO4 and concentrated. 4-(2-{5-[2-(4-Fluoro-phenyl)-2-oxo-ethylamino]-2-methyl-phenyl amino}-oxazol-5-yl)-benzonitrile was obtained after silica gel column chromatography (dichloromethane/ethanol: 9812) (38 mg, 43%) as beige solid.

Provenance & Evidence