[C:1](=[O:4])([O-])[O-].[K+].[K+].CN(C)C=O.O[C:13]1[CH:18]=C[N:16]=[CH:15][CH:14]=1.I[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1>[Cu](I)I.O>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([N:16]2[CH:15]=[CH:14][CH:13]=[CH:18][C:1]2=[O:4])=[CH:21][CH:22]=1
Potassium carbonate (1.16 g, 8.41 mmol) and copper iodide (16 mg, 0.084 mmol) were added to a dimethylformamide (12 mL) solution of 4-hydroxypyridine (800 mg, 8.41 mmol) and 4-iodo-1-methoxybenzene (3.94 g, 16.8 mmol), and stirred at 150° C. for 21 hours. The reaction mixture was cooled to room temperature, then water was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried with anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified through silica gel column chromatography (C-300, hexane/ethyl acetate=1/1) to obtain the entitled compound (870 mg, 51%).
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