N-Iodosuccinimide → 5-Benzyl-4-iodo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole
Reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([C:16]1[CH:37]=[C:36]([O:38][CH3:39])[C:19]2[N:20]([CH2:32][CH2:33][O:34][CH3:35])[C:21]([C:23]3[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:25][CH:24]=3)=[N:22][C:18]=2[CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(#N)C>[CH2:9]([C:16]1[CH:37]=[C:36]([O:38][CH3:39])[C:19]2[N:20]([CH2:32][CH2:33][O:34][CH3:35])[C:21]([C:23]3[CH:28]=[CH:27][C:26]([CH:29]([CH3:31])[CH3:30])=[CH:25][CH:24]=3)=[N:22][C:18]=2[C:17]=1[I:1])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
417 mg (1.78 mmol) N-iodo-succinimide are added to a solution of 670 mg (1.62 mmol) 5-benzyl-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole in 25 ml acetonitrile. The reaction mixture is stirred at reflux temperature for 3 h. The reaction mixture is poured on water and extracted (3×) with ethyl acetate. The combined organic layers are washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=4:1) to afford 582 mg of the title compound as a white crystalline solid.