Br[C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.[N:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:7]([O:6][C:5]1[CH:14]=[CH:15][C:2]([C:22]2[CH:23]=[CH:24][N:19]=[CH:20][CH:21]=2)=[CH:3][C:4]=1[N+:16]([O-:18])=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1To a solution of 1-((4-bromo-2-nitrophenoxy)methyl)benzene 13.B (1.40 g, 4.55 mmol) and pyridin-4-ylboronic acid (665 mg, 5.45 mmol, available from Aldrich) in DMF (10 mL) was added cesium carbonate (2.93 g, 9.0 mmol). The mixture was stirred overnight at 80° C. and then partitioned between AcOEt and water. The organic phase was concentrated to afford 4-(4-(benzyloxy)-3-nitrophenyl)pyridine 13.0 (1.52 g, 109% yield) which was used in the next step without any further purification.
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