[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[O:14][N:13]=[C:12]([NH2:15])[N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[K+].[I:18]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C>[I:18][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:10]3[O:14][N:13]=[C:12]([NH2:15])[N:11]=3)[CH:5]=2)[NH:1][CH:2]=1To a solution of 5-(1H-indol-5-yl)-[1,2,4]oxadiazol-3-ylamine (0.225 g, 1.12 mmol) in DMF (1 mL) was added KOH pellets (0.189 g, 3.36 mmol) at 0-5° C. The reaction was stirred for 10 min then I2 (0.567 g, 2.24 mmol) was added portionwise. The reaction was stirred another 2 h at RT then treated with saturated aq sodium thiosulphate (100 mL) to obtain a brownish precipitate. The precipitate was filtered and dried under vacuum. The crude was further treated with petroleum ether to give 5-(3-iodo-1H-indol-5-yl)-1,2,4-oxadiazol-3-amine (0.2 g, 54%) as off white solid. MS (ESI, pos. ion) m/z: 326.9 (M+1).
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