Sodium hydride → 3-[4-(1-carbomethoxy-1-(3-chlorophenyl)methoxy)-3-chloro-5-propylphenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo-[4,5-b]pyridine

Participants

Reaction Steps

To a solution of 0.085 g (0.49 mmol) of 5,7-dimethyl-2-ethylimidazo[4,5-b]pyridine in 1.0 mL anhydrous DMF was added 21.0 mg (0.54 mmol) of a 60% oil dispersion of sodium hydride and the reaction mixture was stirred under a nitrogen atmosphere at room temperature for 1 hour. A solution of 0.250 g (0.56 mmol) of the product of Step C in 0.5 mL of DMF was added and the reaction was stirred an additional 2 hours at room temperature. The reaction mixture was partitioned between EtOAc and water, separated, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 50% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded 0.150 g (58%) of the title compound.

Provenance & Evidence