Sodium hydride → 3-(2'-cyano-1,1'-biphenyl-4-yl)methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine

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Reaction Steps

To a suspension of 60% NaH (400 mg) in DMF (10 mL) was added the solution of 5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine (1.75 g, 10 mmol) DMF (10 mL) at 0° C. After 5 min, 4-bromomethyl-2'-cyano-1,1'-biphenyl (2.72 g, 10 mmol; Eur. Pat. Appl. 324,377, 1989) in DMF (10 mL) was added at 0° C. and the mixture was stirred at rt for 15 hrs. Extractive workup (2×EtOAc) from water followed by purification of the concentrated organic phases (Si02,) gave 3-(2'-cyano-1,1'-biphenyl-4-yl)methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine as a solid.

Provenance & Evidence