N-Iodosuccinimide → 5-Benzyl-4-iodo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole

HRID 1661917Notes

Reaction equation

HRID 1661917 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]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 577720445-benzyl-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole

Product 1

HCID 113532215-Benzyl-4-iodo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazoleYield 66.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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.

Workup

  1. temperatureat reflux temperature for 3 h
  2. additionThe reaction mixture is poured on water
  3. extractionextracted (3×) with ethyl acetate
  4. washThe combined organic layers are washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=4:1)

Sources & evidence

ORD record
ord-037217a7fe874461a762c3f0290ed7fc
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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