N-Iodosuccinimide → 3-Iodo-5-methoxy-7-phenylimidazo[1,2-a]pyridine

Reaction equation

[CH3:1][O:2][C:3]1[N:8]2[CH:9]=[CH:10][N:11]=[C:7]2[CH:6]=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=1.[I:18]N1C(=O)CCC1=O>C(#N)C.C(OCC)(=O)C>[I:18][C:9]1[N:8]2[C:3]([O:2][CH3:1])=[CH:4][C:5]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:6][C:7]2=[N:11][CH:10]=1

Participants

Procedure

To a solution of 5-methoxy-7-phenylimidazo[1,2-a]pyridine (397 mg, 1.77 mmol) in acetonitrile (30 ml) was added N-iodosuccinimide (478 mg, 2.12 mmol). After 1 h the reaction mixture was diluted with ethyl acetate, washed with 1N aqueous sodium hydroxide and water, then dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/isohexane gradient) to give 3-iodo-5-methoxy-7-phenylimidazo[1,2-a]pyridine. 1H NMR (600 MHz, DMSO-d6) δ 7.86 (d, 1H); 7.83 (d, 1H); 7.52-7.53 (m, 1H); 7.48-7.45 (m, 2H); 7.38-7.40 (m, 1H); 7.33-7.35 (m, 1H); 6.61 (d, 1H); 4.10 (s, 3H). LRMS (ESI) calculated for C14H12IN2O [M+H]+, 351.0 found 350.9.