N-bromobutanimide → 4-Bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbonitrile

HRID 1661910Notes

Reaction equation

HRID 1661910 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:25][CH3:26])=[CH:20][C:21]([C:23]#[N:24])=[CH:22][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Br:27]N1C(=O)CCC1=O>C(#N)C>[Br:27][C:22]1[C:12]2[N:11]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=3)[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]=2[C:19]([O:25][CH3:26])=[CH:20][C:21]=1[C:23]#[N:24]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 112795222-(4-Isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbonitrile

Product 1

HCID 113848354-Bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbonitrileYield 44.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 110 mg (0.315 mmol) 2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbonitrile and 56 mg (0.315 mmol) N-bromosuccinimide in 5 ml acetonitrile is stirred at reflux for 3 h. Then the solvents are evaporated and the residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1) and recrystallized from EtOAc/diethyl ether/hexane to afford 60 mg of the title compound as colorless crystals.

Workup

  1. temperatureat reflux for 3 h
  2. customThen the solvents are evaporated
  3. customthe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1)
  4. customrecrystallized from EtOAc/diethyl ether/hexane

Sources & evidence

ORD record
ord-a2dd1a644d77471ea16d55b4444cc94b
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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