[Br:1][C:2]1[CH:7]=[C:6]([C:8]#[CH:9])[CH:5]=[CH:4][N:3]=1.[CH3:10][O:11][C:12]1[CH:21]=[CH:20][C:15]([CH2:16][N:17]=[N+:18]=[N-:19])=[CH:14][CH:13]=1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].O>CCOC(C)=O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Cu+2].CC(O)(C)C>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[N:19]=[N:18][N:17]([CH2:16][C:15]3[CH:20]=[CH:21][C:12]([O:11][CH3:10])=[CH:13][CH:14]=3)[CH:9]=2)[CH:5]=[CH:4][N:3]=1To a flask containing 2-bromo-4-ethynylpyridine (1 g, 5.49 mmol) was added 4-methoxybenzyl azide (896 mg, 5.49 mmol), CuSO4(H2O)5 (137 mg, 0.549 mmol), sodium ascorbate (544 mg, 2.75 mmol), water (13.7 mL) and tBuOH (13.7 mL) and the reaction was stirred for 16 h at rt. The reaction was diluted with EtOAc (50 mL) and washed with saturated aqueous NaHCO3 (1×20 mL) and brine (1×20 mL). The organic phase was dried (MgSO4), filtered, and purified by silica gel chromatography using a gradient solvent system of 30-70% EtOAc/Hexanes. Concentration of the product fractions yielded 2-bromo-4-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)pyridine (1.46 g, 77%) as a white powder. MS ESI calcd for C15H13BrN4O [M+H]+ 345, found 345.
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