Sodium hydride → 1-Biphenyl-4-ylmethyl-6-chloro-5-iodo-2-methanesulfonyl-1H-benzoimidazole

Participants

Reaction Steps

To a solution of 6-chloro-5-iodo-2-methanesulfonyl-1H-benzoimidazole (1.53 g, 4.3 mmol) in DMF (21 ml) at 0° C. was added sodium hydride (60% dispersion in mineral oil, 190 mg, 4.7 mmol). After 15 minutes, the reaction was warmed to rt and stirred for 1 hour. The mixture was then cooled to 0° C. and 4-bromomethyl-biphenyl (1.2 g, 4.7 mmol) was slowly added. The mixture was then warmed to rt and stirred overnight. The volatiles were removed on a rotary evaporator and the residue was partitioned between EtOAc and half-saturated ammonium chloride. The aqueous layer was extracted a second time and the organic extracts were combined. The combined EtOAc extracts were washed with H2O, brine, and then dried with MgSO4. The crude oil obtained upon rotary evaporation was triturated in Et2O and filtered to yield the title compound as a beige solid.

Provenance & Evidence