Oxalyl chloride → N-(1-benzyl-1H-indazol-4-yl)-6-bromoimidazo[1,2-a]pyridine-3-carboxamide

Participants

Reaction Steps

6-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid (200 mg; 0.83 mmol) was suspended in methylene chloride (2 mL) with a catalytic (0.005 mL) amount of DMF. A solution of oxalyl chloride (0.913 mmol; 2M solution on dichloromethane) was added. The mixture was stirred in a sealed vial (with occasional venting to release gas) until effervescence ceased (about 30 minutes). A white suspension resulted. Diisopropylethylamine (188 μL; 1.08 mmol) was added. A clear solution resulted. 1-Benzyl-1H-indazol-4-amine (185 mg; 0.83 mmol) was added as a solution in methylene chloride followed by addition of further diisopropylethylamine (188 μL). The mixture was stirred at ambient temperature for 24 hours. A suspension resulted. The mixture was diluted with ether (10 mL) and the solids were collected by filtration. The filter pad was washed with ether and water and the solids were dried under vacuum to provide the desired product as a white solid (175 mg). MS (APCI) positive scan, m/z=446, 449 (M+H).

Provenance & Evidence