Oxalyl chloride → N-(1-(2,4-difluorobenzyl)-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide

Participants

Reaction Steps

7-(2-Methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylic acid (0.070 g, 0.296 mmol) and a 2M solution of oxalyl chloride in methylene chloride (0.163 mL, 0.326 mmol) were suspended in methylene chloride (2 mL) with a catalytic amount of DMF. The mixture was stirred for a few minutes and then treated with 1-(2,4-difluorobenzyl)-1H-indazol-4-amine (0.084 g, 0.326 mmol) as a solution in about 1 mL methylene chloride, followed by addition of diisopropylethylamine (0.062 mL, 0.356 mmol). After stirring the mixture overnight, the residue was shaken in water/methylene chloride and suspended solids collected by filtration to provide N-(1-(2,4-difluorobenzyl)-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide (0.070 g, 50% yield). MS (APCI) m/z=478 (M+H).

Provenance & Evidence