C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[C:13]([CH2:15][OH:16])[CH:12]=[CH:11][N:10]=1.CS(Cl)(=O)=O.[F:22][C:23]1[CH:28]=[CH:27][C:26](O)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.CN(C)C=O>[Cl:8][C:9]1[CH:14]=[C:13]([CH2:15][O:16][C:26]2[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=2)[CH:12]=[CH:11][N:10]=1Triethylamine (1.2 mL, 8.4 mmols) was added to a mixture of (2-chloro-4-pyridinyl)methanol (1.0 g, 7.0 mmols), methanesulfonyl chloride (0.6 mL, 7.7 mmols) and ethyl acetate (20 mL) under cooling with ice, and stirred at room temperature for 2 hours. Filtering the reaction liquid, the filtrate was concentrated. To the resulting residue, 4-fluorophenol (0.94 g, 8.4 mmols), potassium carbonate (1.93 g, 14.0 mmols) and N,N-dimethylformamide (20 mL) were added and s at 80° C. for 20 hours. Cooling the reaction liquid to room temperature, ethyl acetate was added thereto, followed by washing with saturated aqueous sodium hydrogencarbonate solution and saturated brine and drying over anhydrous sodium sulfate. Concentrating the solvent under reduced pressure, the residue was purified on silica gel column chromatography (KP-Sil, FLASH 40+M, chloroform) to provide the title compound (845 mg, 51%).
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