[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=O.[Cl:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1.[BH4-].[Na+].O>CO>[Cl:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][CH2:6][C:2]2[NH:3][CH:4]=[CH:5][N:1]=2)=[CH:11][CH:10]=1The solution of 2-imidazolecarboxaldehyde (570 mg, 5.9 mmol) and 4-chloroaniline (756 mg, 5.9 mmol) in methanol (5 ml) was stirred at 60° C. for 4 hours, and allowed to cool to room temperature. To the reaction was added NaBH4 (337 mg, 8.9 mmol), and the mixture was additionally stirred for an hour. Water (20 mL) was added to the reaction, which was extracted with ethyl acetate (50 mL). Organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5% methanol in chloroform) to give the title compound (660 mg, 53%).
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