5-benzyloxy-6-(2-fluorophenoxy)-2-pyrazin-2-yl-1H-benzimidazole → 5-(2-fluorophenoxy)-6-hydroxy-2-pyrazin-2-yl-1H-benzimidazole

HRID 13328Notes

Reaction equation

HRID 13328 reaction equation
C([O:8][C:9]1[C:23]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])=[CH:22][C:12]2[NH:13][C:14]([C:16]3[CH:21]=[N:20][CH:19]=[CH:18][N:17]=3)=[N:15][C:11]=2[CH:10]=1)C1C=CC=CC=1.[H][H]>[OH-].[Pd+2].[OH-].[C].CO.O1CCCC1>[F:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[O:24][C:23]1[C:9]([OH:8])=[CH:10][C:11]2[NH:15][C:14]([C:16]3[CH:21]=[N:20][CH:19]=[CH:18][N:17]=3)=[N:13][C:12]=2[CH:22]=1

Participants

6

Reactant 2

HCID 231455135-benzyloxy-6-(2-fluorophenoxy)-2-pyrazin-2-yl-1H-benzimidazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 1356979845-(2-fluorophenoxy)-6-hydroxy-2-pyrazin-2-yl-1H-benzimidazole

Reagents, catalysts & solvents 3

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

500 mg of 20% palladium hydroxide-carbon catalyst was added to a suspension of 697 mg of 5-benzyloxy-6-(2-fluorophenoxy)-2-pyrazin-2-yl-1H-benzimidazole obtained in Example 250, in 10 ml of methanol and 10 ml of tetrahydrofuran, and the reaction liquid was stirred in a hydrogen atmosphere at room temperature for 1 hour. The catalyst was removed through filtration through Celite, the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent: ethyl acetate) to obtain the entitled compound as a yellow solid.

Workup

  1. customThe catalyst was removed through filtration through Celite
  2. customthe solvent was evaporated away under reduced pressure
  3. customthe residue was purified through silica gel column chromatography (developing solvent: ethyl acetate)

Sources & evidence

ORD record
ord-df04df0ea016440f827d8c46053bc877
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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