C[O:2][C:3]1[C:11]([O:12]C)=[CH:10][C:6]2[N:7]=[CH:8][NH:9][C:5]=2[CH:4]=1.[H-].[Na+].[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1.B(Br)(Br)Br>CCOC(C)=O.C(Cl)Cl>[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:7]2[C:6]3[CH:10]=[C:11]([OH:12])[C:3]([OH:2])=[CH:4][C:5]=3[N:9]=[CH:8]2)=[CH:19][CH:18]=1
To a solution of 5,6-dimethoxybenzimidazole (0.100 g, 0.8 mmol) was added 60% NaH (0.021 g, 0.88 mmol). After stirring for 30 min, the 4-chlorobenzylbromide (0.171 g, 0.8 mmol) was added and the solution was heated to 60° C. for 2 h. The reaction solution was diluted with EtOAc (10 mL) and washed with aqueous saturated NaHCO3 (2×10 mL). The organic layer was dried with Na2SO4 and concentrated in vacuo. To a solution of the crude alkylated intermediate (0.8 mmol) in CH2Cl2 (10 mL) was added 1 M BBr3 in CH2Cl2 (1 mL, 1 mmol). After stirring for 16 h, the solvent was removed in vacuo and the crude product was purified by reverse-phase preparative HPLC to provide 1-(4-chloro-benzyl)-1H-benzoimidazole-5,6-diol.
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