Methylamine → 5-chloro-N-methylpyridine-2-carboxamide

Participants

Reaction Steps

To a stirred solution of 5-chloropyridine-2-carboxylic acid (315 mg, 2.0 mmol) in DCE (2.5 ml) at 20 to 25° C. was added CDI (324 mg, 2.0 mmol) and the mixture was stirred at RT overnight. The reaction mixture was heated to ca. 50° C. and a solution of methylamine in THF (2 M, 5.0 mmol) was added. The resulting mixture was stirred at 50° C. overnight and then cooled to RT and diluted with DCM (20 mL). the reaction mixture was washed with sat. NaHCO3 (10 ml) and the organic layer dried (Na2SO4), filtered and concentrated in vacuo. Purification by silica flash column chromatography (eluting with DCM/MeOH 95:5) provided the title compound as off-white solid (140 mg, 41%).

Provenance & Evidence