3-Iodo-p-toluidine → 2-Chloro-N-(3-iodo-4-methylphenyl)pyridine-4-carboxamide

Participants

Reaction Steps

2-Chloroisonicotinic acid (3.3 g) HATU (8.75 g) DIPEA (10.9 ml) and 3-iodo-4-methylaniline (5.00 g) in DMF (50 ml) were heated under nitrogen for 16 h. The reaction was cooled, the solvent was removed under vacuum and the residue was dissolved in dichloromethane (150 ml). The solution was washed with water (3×100 ml) and brine (100 ml) dried (magnesium sulphate) and the solvent was removed under vacuum. The residue was purified by column chromatography on silica eluting with ethyl acetate/cyclohexane (40:60) to give the title compound as a white solid (7.00 g).

Provenance & Evidence