Isobutylene oxide → 4-Bromo-1-(2-hydroxy-2-methylpropyl)-2(1H)-pyridinone

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-bromopyridin-2(1H)-one (200 mg, 1.15 mmol), 2,2-dimethyloxirane (208 μL, 2.34 mmol) in DMF (2 mL) was added K2CO3 (320 mg, 2.32 mmol) and heated at 120° C. for 30 min in a microwave reactor. The reaction mixture was partitioned between ethyl acetate and water and the layers were separated. The organic extract was dried (Na2SO4), filtered and concentrated to afford a crystalline solid (240 mg, 85% yield) which was used without further purification. 1H NMR (400 MHz, CCl3D) δ 7.25 (d, J=7.5 Hz, 1H), 6.88 (d, J=2.0 Hz, 1H), 6.38 (dd, J=7.3, 2.2 Hz, 1H), 4.01 (s, 2H), 3.43 (br s, 1H), 1.28 (m, 6H).

Provenance & Evidence