Ethyl Acetate → 5-Bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole

HRID 1661904Notes

Reaction equation

HRID 1661904 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:25][CH3:26])[C:5]([NH:20][CH2:21][CH2:22][O:23][CH3:24])=[C:6]([NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:12][CH:11]=2)[CH:7]=1.C(OCC)(=O)C>CC(O)=O>[Br:1][C:2]1[CH:3]=[C:4]([O:25][CH3:26])[C:5]2[N:20]([CH2:21][CH2:22][O:23][CH3:24])[C:9]([C:10]3[CH:15]=[CH:14][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:12][CH:11]=3)=[N:8][C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 57771993N-[5-bromo-3-methoxy-2-(2-methoxy-ethylamino)-phenyl]-4-isopropyl-benzamide

Product 1

HCID 113841195-Bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazoleYield 87.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 748 mg (1.77 mmol) N-[5-bromo-3-methoxy-2-(2-methoxy-ethylamino)-phenyl]-4-isopropyl-benzamide in 10 ml AcOH is stirred at 100° C. for 2 h. The reaction mixture is cooled to room temperature 200 ml ethyl acetate is added. The solution is washed with 4N NaOH (2×) and with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1) to afford 625 mg of the title compound as a colorless solid.

Workup

  1. additionis added
  2. washThe solution is washed with 4N NaOH (2×) and with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1)

Sources & evidence

ORD record
ord-31725b9e45e24864bcbd87c7f7734746
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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