[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7]([NH2:9])=[N:8][C:4]=2[CH:3]=1.F[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br-]>O.CN(C)C(=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([NH2:9])[N:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:4]=2[CH:3]=1To two 10-20 mL microwave vials was added 5-bromo-1H-benzo[d]imidazol-2-amine (3.00 g, 14.1 mmol, Carbocore, The Woodlands, Tex.), N,N-dimethylacetamide (20 mL), 2-fluoropyridine (1.46 mL, 17.0 mmol, Aldrich, St. Louis, Mo.) and cesium carbonate (7.84 g, 24.1 mmol). (One-half of the material in each vial, ie 1.5 g of the bromide in each vial.) The mixture was heated at 150° C. for 140 min in the microwave. After cooling to rt, the combined reaction mixtures were poured into water (400 mL) and then extracted with EtOAc/hexane (80:20) (3×150 mL). The combined extracts were washed with water (3×100 mL) and brine (100 mL) and then dried (Na2SO4) and concentrated onto silica. Purification by silica gel chromatography (0.5 to 3.8% MeOH (2 M in NH3)/CH2Cl2) afforded the title compound (1.06 g, 26%). MS (ESI, positive ion) m/z: 289 (M(79Br)+1).
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