2-Chloro-5-((5-fluoro-4-methylpyridin-3-yl)ethynyl)isonicotinaldehyde oxime → 7-Chloro-3-(5-fluoro-4-methylpyridin-3-yl)-2,6-naphthyridine 2-oxide

Participants

Reaction Conditions

Reaction Steps

A slurry of 2-chloro-5-((5-fluoro-4-methylpyridin-3-yl)ethynyl)isonicotinaldehyde oxime (400 mg, 1.38 mmol) in chloroform (10 mL) was treated with silver nitrate on silica gel (10% w/w, 357 mg, 0.210 mmol). The reaction mixture was heated at 60° C. for 2 hours and then diluted with DCM (20 mL) and methanol (5 mL), loaded on silica gel, and purified by flash chromatography (12 g, Silica, 0-10% methanol in dichloromethane). Desired fractions were combined and evaporated in vacuo to afford the title compound as an off-white solid (270 mg, 66% over two steps). 1H NMR (400 MHz, DMSO) δ 9.20 (s, 1H), 9.14 (s, 1H), 8.65 (s, 1H), 8.40 (s, 2H), 8.01 (s, 1H), 2.12 (s, 3H).

Provenance & Evidence