Sodium hydride → (Z)-3-[(4-(2-carbomethoxy-2-phenylethen-1-yl)phenyl)methyl]-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine

Participants

Reaction Steps

To a solution of 30 mg (0.171 mmol) of 2-propyl-7-methylimidazo[4,5-b]pyridine (Example 2, Step D) dissolved in 1 mL of dry DMF was added 11 mg of a 60% oil dispersion of NaH (1.5 eq) and the reaction mixture was stirred under an N2 atmosphere. After stirring at room temperature for 30 minutes the product from Step C (27.4 mg, 0.082 mmol) dissolved in 0.5 mL DMF was added via syringe. The reaction mixture was quenched with saturated NH4Cl solution, and the solvent was removed under in vacuo. The residue was dissolved in EtOAc and washed with H2O and brine. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 50% ethyl acetate/hexane to provide 13.2 mg (38%) of the title compound.

Provenance & Evidence