Oxalyl chloride → N-(3-methoxy-1-((6-methylpyridin-3-yl)methyl)-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide

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Reaction Steps

A suspension of 7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylic acid (Example 1, Steps A-D; 0.014 g, 0.059 mmol) and 2M oxalyl chloride in DCM solution (0.033 mL, 0.065 mmol) were suspended in DCM (1 mL) with a catalytic amount of DMF. 3-Methoxy-1-((6-methylpyridin-3-yl)methyl)-1H-indazol-4-amine (0.016 g, 0.059 mmol) in DCM (1 mL) was added, followed by diisopropylethylamine (0.012 mL, 0.071 mmol). The mixture was stirred overnight and then was in water-DCM, the organic layer was filtered through glass fiber filter paper, concentrated under reduced pressure and purified by silica gel chromatography (3% MeOH in DCM) to give N-(3-methoxy-1-((6-methylpyridin-3-yl)methyl)-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide (0.014 mg, 49% yield) as a beige solid. MS (APCI) m/z=487 (M+H).

Provenance & Evidence