Sodium hydride → 3-[4-(1-Carboxy-1-(3,4-methylenedioxyphenyl)methoxy)-3,5-dichlorophenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine

Participants

Reaction Steps

To a solution of 0.034 g (0.20 mmol) of 5,7-dimethyl-2-ethylimidazo[4,5-b]pyridine in 0.5 mL anhydrous DMF was added 8.6 mg (0.22 mmol) of a 60% oil dispersion of sodium hydride and the reaction mixture was stirred under a nitrogen atmosphere at room temperature for 30 minutes. A solution of 0.100 g (0.22 mmol) of the product of Step B in 0.9 mL of DMF was added and the reaction was stirred an additional 1.5 hour at room temperature. The reaction mixture was partitioned between EtOAc and 5% aqueous NH4Cl, 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 0.081 g (74%) of the title compound.

Provenance & Evidence