[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C:11]#[C:12][C:13]2[CH:14]=[N:15][CH:16]=[C:17]([F:20])[C:18]=2[CH3:19])=[CH:9][N:10]=1)[CH:5]=[N:6][OH:7]>C(Cl)(Cl)Cl.C(Cl)Cl.CO.[N+]([O-])([O-])=O.[Ag+]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8]([CH:11]=[C:12]([C:13]3[CH:14]=[N:15][CH:16]=[C:17]([F:20])[C:18]=3[CH3:19])[N+:6]([O-:7])=[CH:5]2)=[CH:9][N:10]=1A 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).
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