5-[4-(benzyloxy)biphenyl-3-yl]-1-methyl-1H-pyrazole → 3-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-ol

HRID 1619708Notes

Reaction equation

HRID 1619708 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][C:10]=1[C:21]1[N:25]([CH3:26])[N:24]=[CH:23][CH:22]=1)C1C=CC=CC=1>CO.[Pd]>[CH3:26][N:25]1[C:21]([C:10]2[CH:11]=[C:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:13]=[CH:14][C:9]=2[OH:8])=[CH:22][CH:23]=[N:24]1

Participants

4

Reactant 1

HCID 580422625-[4-(benzyloxy)biphenyl-3-yl]-1-methyl-1H-pyrazole

Product 1

HCID 1362008913-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-olYield 88.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred suspension of 5-[4-(benzyloxy)biphenyl-3-yl]-1-methyl-1H-pyrazole (Preparation 108, 3 g, 8.81 mmol) in methanol (26 mL) was added palladium on carbon (300 mg). The mixture was stirred at room temperature under a hydrogen atmosphere for 16 hours before filtering through a Celite™ pad. The pad was washed with tetrahydrofuran and the filtrate was evaporated in vacuo. The residue was dissolved in ethyl acetate (26 mL) and the solution degassed with argon. Palladium on carbon (300 mg) was added and the mixture was stirred at room temperature under a hydrogen atmosphere for 6 hours. The catalyst was filtered off through a Celite pad and the filtrate was evaporated in vacuo. Trituration of the residue with n-hexane afforded the title compound (1.95 g) as a white solid.

Workup

  1. filtrationbefore filtering through a Celite™ pad
  2. washThe pad was washed with tetrahydrofuran
  3. customthe filtrate was evaporated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (26 mL)
  5. customthe solution degassed with argon
  6. additionPalladium on carbon (300 mg) was added
  7. stirringthe mixture was stirred at room temperature under a hydrogen atmosphere for 6 hours
  8. filtrationThe catalyst was filtered off through a Celite pad
  9. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-5e80dcb6530948e78fbed731d703b006
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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