[Na].[Br:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([OH:10])=[CH:5][C:4]=1[CH3:11].Br[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=1>C(OCC)(=O)C.[Cu]>[Br:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([O:10][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=2)=[CH:5][C:4]=1[CH3:11]To a solution of sodium hydroxide (0.23 g, 5.81 mmol) in methanol (50 mL) was added 4-bromo-3,5-dimethylphenol (1.17 g, 5.81 mmol) and the mixture was left standing at room temperature for 10 min. and concentrated to dryness to give 4-bromo-3,5-dimethylphenol sodium salt (1.30 g). Then, a mixture of the obtained 4-bromo-3,5-dimethylphenol sodium salt (1.30 g), 2-bromo-6-methylpyridine (1.0 g, 5.81 mmol) and copper powder (11 mg, 0.17 mmol) was stirred at 185° C. for 1 hr. The reaction mixture was cooled, diluted with ethyl acetate, washed with water and saturated brine, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-hexane/ethyl acetate=5/1) to give the title compound (1.25 g, yield 74%) as a pale-yellow oil.
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