O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].[C:14]([C:16]1[N:21]=[C:20]([NH2:22])[CH:19]=[CH:18][CH:17]=1)#[CH:15].[CH2:23]([N:30]=[N+:31]=[N-:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O.C(O)C.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:23]([N:30]1[CH:15]=[C:14]([C:16]2[N:21]=[C:20]([NH2:22])[CH:19]=[CH:18][CH:17]=2)[N:32]=[N:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1Sodium ascorbate (34 mg, 0.17 mmol) and copper (II) sulfate pentahydrate (11 mg, 0.042 mmol) were added to a solution of 6-ethynylpyridine-2-amine (100 mg, 0.85 mmol) and benzyl azide (113 mg, 0.846 mmol) in water (5 mL) and ethanol (5 mL). The reaction mixture was stirred vigorously in the absence of light for 14 hours. The reaction mixture was filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10-100% ethyl acetate/hexanes, linear gradient) to afford 6-(1-benzyl-1H-1,2,3-triazol-4-yl)pyridin-2-amine. MS ESI calc'd. for C14H14N5 [M+H]+ 252. found 252. 1H NMR (500 MHz, CD3OD) δ 8.21 (s, 1H), 7.49-7.44 (m, 1H), 7.37-7.26 (m, 5H), 7.22 (d, J=7.4 Hz, 1H), 6.49 (d, J=8.2 Hz, 1H), 5.58 (s, 2H).
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