Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1.[F-:13].[K+].Cl[C:16]([F:22])([F:21])C(OC)=O.[NH4+].[OH-].[NH4+].[Cl-]>CN(C=O)C.[Cu]I>[CH3:12][O:11][C:4]1[N:3]=[C:2]([C:16]([F:22])([F:13])[F:21])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1To a solution of 2-chloro-6-methoxy-3-nitropyridine (0.6 g, 3.2 mmol) in DMF (1.2 mL) were added CuI (0.73 g, 3.8 mmol) and KF (0.37 g, 6.4 mmol), followed by methyl chlorodifluoroacetate (1.15 g, 7.97 mmol). The reaction mixture was heated for 13 h at 120° C. The reaction mixture was then cooled to room temperature and poured onto a mixture of NH4OH and saturated aqueous NH4Cl solution (1:1). The resulting solution was stirred for 1.5 h at room temperature. The organic layer was washed with water and brine, dried over sodium sulphate and concentrated. The crude material obtained was purified by column chromatography (silica: 100-200 mesh, DCM:hexane 3-4%) to afford the title compound (0.5 g, 71%) as a colourless oil. δH (CDCl3) 8.17 (d, J=8.9 Hz, 1H), 7.03 (d, J=8.9 Hz, 1H), 4.09 (s, 3H).
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