Stannane, tributyl(1-ethoxyethenyl)- → 6-(1-ethoxyvinyl)-3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridine (500 mg, 1.83 mmol), tributyl(1-ethoxyvinyl)stannane (866 mg, 2.40 mmol), Pd (PPh3)4 (243 mg, 0.27 mmol) in NMP (10 mL) was heated at 140° C. for 72 h. The reaction mixture was quenched with water and extracted with EtOAc (50 mL×3). The combined extracts were washed with water (100 mL) and brine (50 mL), dried (MgSO4) filtered and concentrated under reduced pressure. The residue was purified by SiO2 chromatography eluting with 3% MeOH/DCM to afford 440 mg (78%) of 6-(1-ethoxyvinyl)-3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridine as a gray solid. MS (EST): m/z=310.3 [M+1]+.

Provenance & Evidence