N-methyl-2-pyrrolidone → cyano-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Participants

Reaction Steps

Lithium 6-cyanoimidazo[1,2-a]pyridine-3-carboxylate (107 mg, 0.6 mmol) was dissolved in anhydrous NMP (2.8 mL) and 2,4,6-trichlorobenzoyl chloride (94 mL, 0.6 mmol) was added dropwise. The mixture was stirred at ambient temperature for 30 minutes. 3-Ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine (137 mg, 0.5 mmol) was added in one portion and the reaction mixture was heated to 80° C. for 6 hours. Saturated sodium bicarbonate solution was added until a precipitate formed and the mixture was allowed to stir at ambient temperature for 1 hour. The precipitate was collected by filtration and dried under high vacuum for 2 hours to give cyano-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide as a beige solid (147 mg). MS m/z 436.3 (M+1, APCI+).

Provenance & Evidence