Sodium hydride → 2-[1-(4-bromo-2-fluorobenzyl)-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl]benzonitrile

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Reaction Steps

A solution of 2-(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)benzonitrile (6-4, 20 mg, 0.08 mmol) in anhydrous DMF (1 ml) was charged with Sodium Hydride (6.42 mg, 0.16 mmol, 2.0 eq) and 4-Bromo-2-fluorobenzyl bromide (42.5 mg, 0.16 mmol, 2.0 eq). The resulting dark mixture was irradiated in a microwave at 200 deg C. for 15 min, then quenched with water, filtered and purified via reverse-phase HPLC (Acetonitrile/Water gradient with 0.1% TFA present) to afford the title compound, 2-[1-(4-bromo-2-fluorobenzyl)-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl]benzonitrile (6-5), as an orange-tan solid-oil. LRMS m/z: Calc'd for C22H15BrFN3O (M+H) 436.0, found 435.9.

Provenance & Evidence