Oxalyl chloride → N-(3-Ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

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Reaction Steps

To a stirred suspension of imidazo[1,2-a]pyridine-3-carboxylic acid (36.5 mg, 0.225 mmol) in dichloromethane (0.6 mL) was added N,N-dimethylformamide. Oxalyl chloride (84.5 μL, 0.169 mmol) was added and the mixture was stirred in a sealed vessel with ice cooling. The cooling was removed and the mixture was stirred for 3 hours with occasional venting to allow gases to escape. Diisopropylethylamine (21.6 μL, 0.124 mmol) and 3-ethyl-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine (30 mg, 0.113 mmol) were added. The mixture was stirred for 30 minutes and then concentrated under reduced pressure. The material was purified using preparative thin layer chromatography, eluting with 10% methanol in dichloromethane containing 0.5% ammonium hydroxide solution. A second purification eluting with 5% methanol in ethyl acetate containing 0.5% ammonium hydroxide solution was carried out to provide N-(3-Ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (12.5 mg). MS (APCI), positive scan, m/z=411.3 (M+H).

Provenance & Evidence