Ethyl bromoacetate → ethyl 2-(5-bromo-2-oxopyridin-1(2H)-yl)acetate

Participants

Reaction Conditions

Reaction Steps

To an ice-cold solution of 5-bromo-2(1H)-pyridone (1.0 g, 5.75 mmol) in DMF (5.0 mL) was added NaH (60% suspension in mineral oil, 0.25 g, 10.30 mmol) portion wise and the resulting solution was heated to 80° C. for 90 min. The reaction mixture was then again cooled to 0° C. followed by addition ethyl bromoacetate (1.92 g, 11.50 mmol). The reaction mixture was then heated to 80° C. for 16 h. After the completion of reaction (TLC monitoring), DMF was distilled off, added water and extracted with EtOAc (3×100 mL). The combined organics was dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was purified over silica gel (100-200 M, 20% EtOAc-hexane) to obtain the desired product (0.90 g, 60%). MS: 260.10 (M+H)+.

Provenance & Evidence