Under argon protection, 4-bromo-2-hydroxypyridine (1.00 g, 5.75 mmol) was dissolved in THF (20 mL) and cooled to 0°C. Sodium hydride (60% dispersion in mineral oil, 230 mg, 5.75 mmol) was slowly added to this solution and stirred for 30 min at room temperature. Subsequently, ethyl iodide (1.39 mL, 17.25 mmol) was added and the reaction mixture was stirred at room temperature for 16 hours and then heated at 50°C for 24 hours. After completion of the reaction, the mixture was diluted with water and ethyl acetate. The organic layer was separated, washed sequentially with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Finally, the residue was purified by silica gel column chromatography (eluent: DCM/EtOAc, 100/0 to 85/15) to afford the target product 4-bromo-1-ethylpyridin-2(1H)-one (981 mg, 4.86 mmol, 84% yield).
