Hydrochloric Acid → 4-Bromo-2-(4-isopropyl-phenyl)-7-methoxy-5-(3-methoxy-benzyl)-1-(2-methoxy-ethyl)-1H-benzoimidazole

HRID 1661928Notes

Reaction equation

HRID 1661928 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=3)[N:7]([CH2:20][CH2:21][O:22][CH3:23])[C:6]=2[C:5]([O:24][CH3:25])=[CH:4][C:3]=1[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=1)=O.[OH-].[K+].O.NN.Cl>O>[Br:1][C:2]1[C:10]2[N:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:15][CH:16]=3)[N:7]([CH2:20][CH2:21][O:22][CH3:23])[C:6]=2[C:5]([O:24][CH3:25])=[CH:4][C:3]=1[CH2:26][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 11191900[4-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-(3-methoxy-phenyl)-methanone

Product 1

HCID 113414244-Bromo-2-(4-isopropyl-phenyl)-7-methoxy-5-(3-methoxy-benzyl)-1-(2-methoxy-ethyl)-1H-benzoimidazoleYield 16.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 125 mg (0.233 mmol) [4-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-(3-methoxy-phenyl)-methanone (example 26o), 45 mg KOH pellets, 3.2 ml hydrazine-monohydrate, 0.5 ml water and 13 ml ethyleneglykol is stirred at 190° C. for 2 h. After that the reaction mixture is poured on 4N HCl-solution and extracted (3×) with ethyl acetate. The combined organic layers are washed with water (2×) 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 20 mg of the title compound as an off-white crystalline solid.

Workup

  1. extractionextracted (3×) with ethyl acetate
  2. washThe combined organic layers are washed with water (2×) 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-b498885cef1c44b29f27e2819a9f2668
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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