[Cl:1][C:2]1[C:7]([F:8])=[C:6](I)[CH:5]=[CH:4][N:3]=1.[Cl:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[C:12]=1[C:13]([NH2:15])=[O:14].C(N)CN.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[Cl:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[C:12]=1[C:13]([NH:15][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:7]=1[F:8])=[O:14]A mixture of 2-chloro-3-fluoro-4-iodopyridine (4.78 g, 18.6 mmol), 2-chloro-6-nitrobenzamide (3.91 g, 19.5 mmol), ethane-1,2-diamine (0.2 mL, 2.97 mmol), copper(I) iodide (0.57 g, 2.97 mmol) and K3PO4 (7.90 g, 37.2 mmol) in dioxane (80 mL), was degassed with a stream of argon and the reaction mixture was then heated under reflux for 4 hours. After cooling to room temperature, the crude reaction mixture was filtered through Celite® washing with dioxane. The filtrate was concentrated to dryness under reduced pressure and the resultant residue was purified by column chromatography on silica gel eluting with 0-100% ethyl acetate in petroleum ether (40-60° C.), to afford the title compound as a pale yellow solid (1.87 g, 31% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.42-11.37 (br s, 1H), 8.35-8.24 (m, 3H), 8.08 (dd, J=1.1, 8.1 Hz, 1H), 7.81 (t, J=8.2 Hz, 1H).
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