Ethyl bromoacetate → Ethyl {[1-[(4-chlorophenyl)methyl]-2-(1-methylethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-7-yl]oxy}acetate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of Intermediate 58 (55 mg) in anhydrous tetrahydrofuran (3 mL) at 0° C. under an atmosphere of nitrogen was added sodium hydride (10 mg) as a 60% by weight suspension on mineral oil in one charge. The reaction was stirred at 0° C. for 30 min. To the reaction was added neat ethyl bromoacetate (0.026 mL) in one charge the reaction was then allowed to warm to ambient temperature under an atmosphere of nitrogen over 30 min. The reaction was quenched with saturated aqueous ammonium chloride (5 mL) and extracted with ethyl acetate (10 mL). The extract was dried (hydrophobic frit) and concentrated in vacuo. The sample was loaded in dichloromethane and purified on silica using a 0-25% methanol-dichloromethane gradient. The appropriate fractions were combined and evaporated in vacuo to provide the title compound (14 mg). LC/MS MH+ 391, Rt 1.84 min (5 min run).

Provenance & Evidence