[F:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[C:6]([F:11])[C:7]=1[N+:8]([O-:10])=[O:9].C([O-])([O-])=O.[Cs+].[Cs+].Cl.Cl[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][N:23]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:11])[C:7]=1[N+:8]([O-:10])=[O:9])[O:12][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][N:23]=1
To 3,5-difluoro-4-nitrophenol (7.44 g, 42.5 mmol), Cs2CO3 (27.7 g, 84.9 mmol), and 2-(chloromethyl)-5-methylpyridine hydrochloride (7.6 g, 42.5 mmol) was added DMF (281 mL) and the reaction was stirred at 75° Celsius for 18 hours. The reaction was allowed to cool to room temperature before being poured into sat. NaHCO3. The aqueous phase was extracted three times with EtOAc, and the combined organic layers were washed four times with brine, dried (Na2SO4), filtered, and concentrated. The crude material was purified via FCC to afford the title compound. MS (ESI): mass calcd. for C13H10F2N2O3, 280.1; m/z found, 281.0 [M+H]+.
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