Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([Cl:16])[CH:11]=2)[N:4]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[Cl:16][C:12]1[CH:11]=[C:10]([O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][O:24][C:21]3[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=3)[N:4]=2)[CH:15]=[CH:14][N:13]=1A mixture of 2-(chloromethyl)-6-[(2-chloro-4-pyridyl)oxy]pyridine (1.66 g, 6.5 mmol), 4-fluorophenol (0.89 g, 8 mmol), and potassium carbonate (1.1 g, 8 mmol) in N,N-dimethylformamide (5 mL) is refluxed for 90 minutes, cooled, and diluted with a 1:1 hexane/ethyl acetate solution (100 mL). The organic mixture is then filtered through a layer of silica gel using a 1:1 hexane/ethyl acetate solution as eluent. The resultant solution is concentrated in vacuo to obtain an oil. Flash column chromatography of the oil using silica gel and a 8:2 hexane/ethyl acetate solution gives the title product as colorless crystals (1.5 g, 70%, mp 103° C.).
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