Cl[CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=2)[CH:7]=1.[N-:15]=[N+:16]=[N-:17].[Na+].O.CCOC(C)=O>CN(C=O)C>[N:15]([CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=2)[CH:7]=1)=[N+:16]=[N-:17]The compound 4-(chloromethyl)-1-(4-iodophenyl)-1H-imidazole 9.5 (0.780 g, 2.45 mmol) was dissolved in DMF (10 mL). To the solution, NaN3 (0.520 g, 8.00 mmol) was added. After being stirred at room temperature overnight, water and EtOAc were added. The organic layer was separated, dried over Na2SO4, concentrated in vacuo to give 4-(azidomethyl)-1-(4-iodophenyl)-1H-imidazole 9.6 as a solid (0.725 g). MS 326.0 (M+H).
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