[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[CH:6]2)#[CH:2].I[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[Na+].[Na+].[N-:33]=[N+:34]=[N-:35].[Na+].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CS(C)=O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[C:13]1([N:33]2[CH:2]=[C:1]([C:3]3[CH:4]=[C:5]4[C:9](=[CH:10][CH:11]=3)[NH:8][N:7]=[CH:6]4)[N:35]=[N:34]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1To a solution of Example 1C (30 mg, 0.21 mmol) in dimethyl sulfoxide (0.25 mL) was added iodobenzene (0.024 mL, 0.21 mmol), a solution of L-proline (5 mg, 0.042 mmol) and sodium carbonate (5 mg, 0.04 mmol) in water (0.1 mL), sodium azide (16 mg, 0.25 mmol), a solution of sodium ascorbate (8 mg, 0.04 mmol) in water (0.05 mL) and a solution of copper (II) sulfate pentahydrate (6 mg, 0.02 mmol) in water (0.05 mL) and the mixture was heated at 65° C. overnight. The mixture was centrifuged, and the crude solids were washed with methanol. The methanol wash was removed with a pipette. It was then dissolved in dimethyl sulfoxide and passed through a silica gel plug eluting with ethyl acetate. The product containing fractions were combined, concentrated in vacuo, and then treated with water. The mixture was centrifuged, and the solid was washed with water and methanol. The washes were removed with a pipette affording the title compound. 1H NMR (400 MHz) δ ppm 13.17 (s, 1H), 9.28 (s, 1H), 8.34 (s, 1H), 8.17 (s, 1H), 7.96 (m, 3H), 7.65 (m, 3H), 7.52 (m, 1H). MS (ESI) m/z 262 (M+H).
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