[Br:1][C:2]1[CH:12]=[CH:11][C:5]2[N:6]([CH3:10])[C:7](=[O:9])[NH:8][C:4]=2[C:3]=1[O:13][CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O.C(OCC)(=O)C.O>[CH2:21]([N:8]1[C:4]2[C:3]([O:13][CH3:14])=[C:2]([Br:1])[CH:12]=[CH:11][C:5]=2[N:6]([CH3:10])[C:7]1=[O:9])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
A solution of 5-bromo-4-methoxy-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (60.0 mg, 0.233 mmol) in N,N-dimethylformamide (2.31 mL) was treated with cesium carbonate (380 mg, 1.17 mmol) and benzyl bromide (99.8 mg, 0.583 mmol) and stirred at 60° C. for 30 min. The reaction mixture was diluted with ethyl acetate and water. Layers were separated and the organic layer was washed with brine, dried with magnesium sulfate, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (15% EtOAc/hexanes to 40% EtOAc/hexanes) gave the desired product (73 mg, 90%). LCMS calculated for C16H16BrN2O2 (M+H)+: m/z=347.1, 349.1. found: 347.0, 349.0.
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