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

HRID 1661913Notes

Reaction equation

HRID 1661913 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:34][CH3:35])=[CH:20][C:21]([CH:23](OC(=O)C)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:22][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].CO>C1COCC1.[Pd]>[CH2:23]([C:21]1[CH:20]=[C:19]([O:34][CH3:35])[C:13]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:10]([C:7]3[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=3)=[N:11][C:12]=2[CH:22]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 57772027Acetic acid[2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1h-benzoimidazol-5-yl]-phenyl-methyl ester

Product 1

HCID 577720445-benzyl-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazoleYield 91.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 150 mg (0.317 mmol) acetic acid[2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-phenyl-methyl ester in 8 ml THF:MeOH=1:2 is hydrogenated in the presence of 50 mg Pd/C (Engelhard 4505). Then the catalyst is filtered off and the filtrate is concentrated in vacuo to afford 120 mg of the title compound as a colorless oil.

Workup

  1. filtrationThen the catalyst is filtered off
  2. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-65d88e20a8784728ab4021f8c58a3639
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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