Ethyl bromoacetate → Ethyl (3-acetyl-4-bromo-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate

Participants

Reaction Steps

Sodium hydride (353 mg of a 60% dispersion in mineral oil, 8.84 mmol) and ethyl bromoacetate (1.15 mL, 8.84 mmol) were added to a solution of 1-acetyl-7-bromo-1,3-dihydro-2H-benzimidazol-2-one from Step B (1.5 g, 5.89 mmol) in DMP (20 mL) at 0° C. After 4 h, the reaction mixture was quenched with brine and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered, and concentrated. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2::EtOAc—100:0 to 80:20, to give the title compound. MS: m/z=343 (M+1).

Provenance & Evidence