Oxalyl chloride → N-(1-Benzyl-3-iodo-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide

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Reaction Steps

7-(2-M ethoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylic acid (150 mg; 0.635 mmol) was suspended in methylene chloride (2 mL), with stirring, under an atmosphere of dry nitrogen. Oxalyl chloride (0.698 mmol) was added as a 2N solution in dichloromethane (0.35 mL). A catalytic amount of dimethylformamide (1 drop) was added. The mixture was stirred until effervescence had ceased (30 minutes). 1-Benzyl-3-iodo-1H-indazol-4-amine (product of step G) (222 mg; 0.635 mmol) was added as a solution in dichloromethane (2 mL). Diisopropylethylamine (213 mg; 0.29 mL; 1.65 mmol) was added and the mixture was stirred under nitrogen in a sealed vessel for 24 hours. A thick suspension formed. The mixture was diluted with diethyl ether (20 mL) and the solids were collected by filtration. The solids were washed with ether and water and then dried under vacuum. This gave the desired product, N-(1-Benzyl-3-iodo-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide, as an off white solid (139 mg). MS (APCI), positive scan, m/z=568.1 (M+H).

Provenance & Evidence