Thionyl Chloride → N-(3-ethyl-1-((6-methoxypyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

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To imidazo[1,2-a]pyridine-3-carboxylic acid (194 mg, 1.20 mmol) in DCM (5 mL) was added thionyl chloride (2 mL). The reaction mixture was stirred for 2 hours and concentrated to give crude acylchloride HCl salt, to which DCE/THF (2 mL/2 mL) and 3-ethyl-1-((6-methoxypyridin-2-yl)methyl)-1H-indazol-4-amine (211 mg, 0.747 mmol) was added. The reaction mixture was heated to 70° C. and stirred for 1 hour. The reaction mixture was diluted with DCM (20 mL) and washed with saturated NaHCO3 aqueous solution. The organic solution was dried over Na2SO4, filtered and concentrated. Silica gel chromatography (DCM/MeOH 10:1) provided the desired product (226 mg). MS (ES+APCI) m/z=427 (M+H).

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