Ethyl Acetate → 4-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1H-benzoimidazole

HRID 1661885Notes

Reaction equation

HRID 1661885 reaction equation
[NH2:1][C:2]1[C:7]([Br:8])=[CH:6][CH:5]=[C:4]([O:9][CH3:10])[C:3]=1[NH:11][C:12](=O)[C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=1.C(OCC)(=O)C>C(O)(=O)C>[Br:8][C:7]1[C:2]2[N:1]=[C:12]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=3)[NH:11][C:3]=2[C:4]([O:9][CH3:10])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 57772045N-(2-amino-3-bromo-6-methoxy-phenyl)-4-isopropyl-benzamide

Product 1

HCID 577720154-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1H-benzoimidazoleYield 81.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1.44 g (3.97 mmol) N-(2-amino-3-bromo-6-methoxy-phenyl)-4-isopropyl-benzamide in 25 ml glacial acetic acid is stirred at 100° C. for 3 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=2:1) to afford 1.12 g of the title compound as slightly reddish 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=2:1)

Sources & evidence

ORD record
ord-90f93b73bc2d435d8c4201fe6b99079d
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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