[Br:1][C:2]1[CH:3]=[C:4]([NH2:13])[C:5]([NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:6][CH:7]=1.[CH3:14][C:15]1[N:19]=[C:18]([C:20]2[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=2[CH:22]=O)[O:17][N:16]=1.OOS([O-])=O.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([C:9]([CH3:10])([CH3:12])[CH3:11])[C:22]([C:21]3[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=3[C:18]3[O:17][N:16]=[C:15]([CH3:14])[N:19]=3)=[N:13][C:4]=2[CH:3]=1To a solution of 4-bromo-N1-tert-butyl-benzene-1,2-diamine (700 mg, 2.8 mmol) in DMF (15 mL) is added 2-(3-methyl-1,2,4-oxadiazol-5-yl)benzaldehyde (813 mg, 4.3 mmol) at room temperature. Oxone (1.7 g, 2.8 mmol) in H2O (4 mL) is added and the solution is stirred for 1 hour. Saturated sodium thiosulfate solution (10 mL) is added and the mixture is extracted with EtOAc (3×10 mL) and H2O (10 mL). The combined organic layer is dried, (MgSO4), filtered and concentrated. The residue is purified by silica gel flash column chromatography eluting with 10% MeOH in CH2Cl2 to afford the 5-bromo-1-tert-butyl-2-[2-(3-methyl-1,2,4-oxadiazol-5-yl)-phenyl]-1H-benzimidazole (900 mg, 76%) as a pale brown solid.
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