Water → 4-Bromo-1-methylpyridin-2(1H)-one

Participants

Reaction Steps

To an ice-cold solution of 2-hydroxy-4-bromopyridine (1.0 g, 5.75 mmol) in THF (20.0 mL) was added NaH (60% suspension in mineral oil, 0.23 g, 5.75 mmol) portionwise. The reaction mixture was stirred at room temperature for 15 min followed by addition of methyl iodide (1.10 mL, 17.24 mmol). The resulting reaction mixture was stirred at room temperature for 16 h. After the completion of the reaction (TLC monitoring), the reaction mixture was cooled to 0° C., added water and extracted with EtOAc (3×50 mL). The combined organics was washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to obtain the desired product (0.99 g, 92%). 1H NMR (400 MHz, DMSO-d6): δ 3.38 (s, 3H), 6.44 (dd, J=2.0 and 7.20 Hz, 1H), 6.69 (d, J=2.0 Hz, 1H) and 7.69 (d, J=7.20 Hz, 1H).

Provenance & Evidence