[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[H-].[Na+].Br[C:14]1[C:19]([O:20][CH2:21][CH2:22][CH3:23])=[CH:18][CH:17]=[C:16]([I:24])[N:15]=1.O>CN(C)C=O>[I:24][C:16]1[N:15]=[C:14]([O:8][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:19]([O:20][CH2:21][CH2:22][CH3:23])=[CH:18][CH:17]=14-Methoxybenzyl alcohol (689 mg) was added to a solution of sodium hydride (200 mg) in N,N-dimethylformamide (4 mL) under ice-cooling, and the mixture was stirred at room temperature for 15 minutes. A solution of 2-bromo-6-iodo-3-propoxypyridine in N,N-dimethylformamide (2 mL) was added thereto, and the mixture was stirred at 85° C. for six hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1→1:1) to give the title compound as a colorless powder (670 mg).
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