4-{(E)-3-cyclohexyl-3-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-propenyl}-benzoic acid methyl ester → 4-{3-Cyclohexyl-3-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-propyl}-benzoic acid methyl ester

HRID 417168Notes

Reaction equation

HRID 417168 reaction equation
[CH3:1][O:2][C:3](=[O:40])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[CH:12]([CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)[N:13]2[C:17]3[CH:18]=[C:19]([F:23])[C:20]([F:22])=[CH:21][C:16]=3[N:15]=[C:14]2[C:24]2[C:25]([O:32][CH3:33])=[N:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)=[CH:6][CH:5]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:40])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH:12]([CH:34]2[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]2)[N:13]2[C:17]3[CH:18]=[C:19]([F:23])[C:20]([F:22])=[CH:21][C:16]=3[N:15]=[C:14]2[C:24]2[C:25]([O:32][CH3:33])=[N:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 666194594-{(E)-3-cyclohexyl-3-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-propenyl}-benzoic acid methyl ester

Product 1

HCID 666194954-{3-Cyclohexyl-3-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-propyl}-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 210 mg (0.383 mmol) 4-{(E)-3-cyclohexyl-3-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-propenyl}-benzoic acid methyl ester in 4 ml methanol was added 30 mg Pd on carbon 5%. The reaction mixture was hydrogenated at 1.5 bar under vigorous stirring for 1 hour, then filtered over dicalite and concentrated under vacuum. Colorless oil (90%). MS (Turbo Spray): m/z=550.4 [M+H].

Workup

  1. filtrationfiltered over dicalite
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1d18229c3bc94faf882c5ca21b644fc6
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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