I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[NH:11]1[CH:15]=[N:14][CH:13]=[N:12]1.C([O-])([O-])=O.[K+].[K+].N1CCC[C@H]1C(O)=O.CNCCNC>CN(C=O)C.[Cu]I>[N:11]1([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)[CH:15]=[N:14][CH:13]=[N:12]1To a stirred solution of 5-iodo-1H-indole (2.0 g, 8.2 mmol), 1H-1,2,4-triazole (0.511 g, 7.4 mmol), CuI (0.15 g, 0.82 mmol), K2CO3 (2.27 g, 16.46 mmol) and L-proline (0.511 g, 7.4 mmol) in DMF (20 mL), N,N′-dimethylethylenediamine (2.375 g 16.46 mmol) was added and stirred at 120° C. for 2-3 h. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was separated, concentrated in vacuo and the residue was purified by flash column chromatography to give 5-(1H-1,2,4-triazol-1-yl)-1H-indole (0.790 g, 52%); MS: 185 (M+1).
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