Triethylamine → 7-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Participants

Reaction Steps

To a stirred mixture of 7-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)imidazo[1,2-a]pyridine-3-carboxylic acid (128 mg, 0.44 mmol) in tetrahydrofuran (6 mL), under nitrogen, was added 2,4,6-trichlorobenzoyl chloride (115 mg, 0.47 mmol) and triethylamine (51 mg, 0.51 mmol). The mixture was stirred for 30 minutes. To the reaction mixture was added 3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine (90 mg, 0.34 mmol), followed by lithium bis(trimethylsilyl)amide (1.7 mL, 1.7 mmol; 1M solution in tetrahydrofuran). The mixture was concentrated under reduced pressure and purified by flash chromatography on silica, eluting with dichloromethane/methanol (10:1) to give 7-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (30 mg).

Provenance & Evidence