Hexane → N-methoxy-N-methylimidazo[1,2-a]pyridine-7-carboxamide

Participants

Reaction Steps

To a solution of Imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester (0.67 g, 3.83 mmol) and dimethylhydroxylamine (0.93 g, 9.57 mmol) in CH2Cl2 (40 ml) at 0° C. was added 2M trimethylaluminium solution in hexane (3.8 ml, 9.57 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 1 h, before being cooled back to 0° C. and quenched with ice. The reaction was filtered and liquid fraction partitioned between CH2Cl2/H2O. The organic layer was separated, dried (MgSO4), filtered and the solvent removed in vacuo to afford the crude product. The residue was purified by silica column chromatography (0-50% MeOH in Et2O) to afford the product (187 mg). MS: [M+H]+=206.

Provenance & Evidence