Potassium Carbonate → 2-Methyl-(1,2,4)triazolo(1,5-a)pyridine-5-carboxylic acid

Participants

Reaction Steps

To a solution of 5-iodo-2-methyl[1,2,4]triazolo[1,5-a]pyridine (13.5 g, 52.1 mmol) in methanol (521 mL) were added palladium acetate (1.17 g, 5.21 mmol), potassium carbonate (21.6 g, 156 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (2.15 g, 5.21 mmol), and the mixture was stirred under carbon monoxide atmosphere at 2 atm at room temperature for 1 hr. The mixture was warmed to 50° C. and stirred for 12 hr. The reaction mixture was filtered through celite. The solvent was evaporated under reduced pressure. The residue was dissolved in water (300 mL), washed with chloroform, and 2 M hydrochloric acid was added to adjust the solution to pH 2. The aqueous layer was evaporated under reduced pressure, the residue was dissolved in methanol, and insoluble material was filtered off. The solvent was evaporated under reduced pressure to give 2-methyl[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid as a crudely purified product.

Provenance & Evidence