5-benzyl-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-4-vinyl-1H-benzoimidazole → 5-Benzyl-4-ethyl-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole

HRID 1661926Notes

Reaction equation

HRID 1661926 reaction equation
[CH2:1]([C:8]1[CH:29]=[C:28]([O:30][CH3:31])[C:11]2[N:12]([CH2:24][CH2:25][O:26][CH3:27])[C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]([CH3:23])[CH3:22])=[CH:17][CH:16]=3)=[N:14][C:10]=2[C:9]=1[CH:32]=[CH2:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Ni]>[CH2:1]([C:8]1[CH:29]=[C:28]([O:30][CH3:31])[C:11]2[N:12]([CH2:24][CH2:25][O:26][CH3:27])[C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]([CH3:23])[CH3:22])=[CH:17][CH:16]=3)=[N:14][C:10]=2[C:9]=1[CH2:32][CH3:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 577720835-benzyl-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-4-vinyl-1H-benzoimidazole

Product 1

HCID 112129125-Benzyl-4-ethyl-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazoleYield 45.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 58 mg (0.13 mmol) 5-benzyl-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-4-vinyl-1H-benzoimidazole in 5 ml methanol is hydrogenated in the presence of 10 mg Raney-Nickel (B113W Degussa) at normal pressure for 25 h. The catalyst is filtered off and the filtrate is concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=6:1) to afford 26 mg of the title compound as a white crystalline solid.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=6:1)

Sources & evidence

ORD record
ord-24854b9adbba4ece8181d00728f31030
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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