Br[C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.C([Li])(C)(C)C.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][C:15]=1[CH:26]=[O:27].[Cl-].[NH4+]>C1COCC1.CCCCC>[NH:5]1[CH:6]=[C:2]([CH:26]([C:15]2[CH:16]=[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:18]=[CH:19][C:14]=2[O:13][CH3:12])[OH:27])[N:3]=[CH:4]1
4-Bromo-1H-imidazole (5.20 g) was dissolved in THF (50 ml) and the mixture was cooled to −78° C. A solution (1.7 M; 50 ml) of t-butyllithium in pentane was added. The mixture was stirred at 0° C. for 1.5 h and cooled to −78° C. again. A solution (30 ml) of 4-methoxy[1,1′-biphenyl]-3-carbaldehyde (2.54 g) in THF was added, and the mixture was heated from −78° C. to room temperature and further stirred at room temperature for 24 h. Aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The organic layer was dried and concentrated. The residue was purified by silica gel column chomatography (eluent, dichloromethane:methanol=15:1) and recrystallized from ethyl acetate to give the title compound (1.15 g) as a colorless solid.
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