Methyl Methacrylate → HCID 23321871, compound

Participants

Reaction Steps

A solution of 0.34 g of 5-(p-bromophenyl)imidazo[1,5-a]pyridine, 2.7 mg of palladium acetate, 7.5 mg of tri-o-tolyphosphine and 0.22 g methyl methacrylate in 3 ml of triethylamine is refluxed for 7 days, diluted with 50 ml of methylene chloride and washed with water. The methylene chloride is evaporated and the residue is taken up in 50 ml ether, filtered and washed with 2×20 ml of ice-cold 0.5N hydrochloric acid. The aqueous phase is adjusted to pH=8 and is extracted with methylene chloride. The methylene chloride extract is dried over magnesium sulfate and evaporated. Preparative thin layer chromatography (silica gel, ether) yields 5-[p-(2-carbomethoxyprop-2-enyl)phenyl]imidazo[1,5-a]pyridine; Rf=0.37; NMR: (CDCl3) 5.62 (s, 1H), 6.32 (s, 1H); IR (CH2Cl2) 1720 cm-1.

Provenance & Evidence