Phenylacetylene → 6-Phenylethynyl-pyridine-2-carboxylic acid

Participants

Reaction Steps

To a stirring solution 0.5 g (2.4 mmol) of 6-bromo-pyridine-2-carboxylic acid, 0.05 g (0.07 mmol) of dichlorobis(triphenylphosphine)-palladium(II), and 0.015 g (0.07 mmol) of copper (I) iodide in 10 mL of NEt3, 9.9 mL of 2 N Na2CO3 solution was added 0.38 g (3.7 mmol) of phenyl acetylene under nitrogen. After 12 h reflux under nitrogen, the reaction mixture was cooled and filtered. The filtrate was acidified using 2 N HCl (pH=5), and the resulting white precipitate was filtered, washed with water and dried to afford 0.5 g (51%) of 6-phenylethynyl-pyridine-2-carboxylic acid. LCMS: 224 (M+1)+.

Provenance & Evidence