N-Iodosuccinimide → 5-bromo-4-iodo-2-(4-isopropylphenyl)-7-methoxy-1-(2-methoxyethyl)-1H-benzo[d]imidazole

HRID 1661906Notes

Reaction equation

HRID 1661906 reaction equation
[Br:1][C:2]1[CH:23]=[C:22]([O:24][CH3:25])[C:5]2[N:6]([CH2:18][CH2:19][O:20][CH3:21])[C:7]([C:9]3[CH:14]=[CH:13][C:12]([CH:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1.[I:26]N1C(=O)CCC1=O>C(#N)C>[I:26][C:3]1[C:4]2[N:8]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([CH:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=3)[N:6]([CH2:18][CH2:19][O:20][CH3:21])[C:5]=2[C:22]([O:24][CH3:25])=[CH:23][C:2]=1[Br:1]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 113841195-Bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole

Product 1

HCID 111917705-bromo-4-iodo-2-(4-isopropylphenyl)-7-methoxy-1-(2-methoxyethyl)-1H-benzo[d]imidazoleYield 62.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 100 mg (0.248 mmol) 5-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole and 61 mg (0.273 mmol) N-iodosuccinimide in 3 ml acetonitrile is refluxed for 12 h. The reaction mixture is cooled to room temperature and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=4:1) and recrystallisation from hexane/diethyl ether afforded 82 mg of the title compound as colorless crystals.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=4:1) and recrystallisation from hexane/diethyl ether

Sources & evidence

ORD record
ord-5362345c35d244ea8e5eaff324251303
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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