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

HRID 1619643Notes

Reaction equation

HRID 1619643 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 77.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 5-[4-(benzyloxy)biphenyl-3-yl]-1-methyl-1H-pyrazole (Preparation 27, 3.0 g, 8.8 mmol) in methanol (26 mL) was added palladium on carbon (300 mg). The mixture was stirred under hydrogen gas for 16 hours. The reaction mixture was filtered through Celite™, and washed with tetrahydrofuran. The resulting filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate (26 mL) and degassed with argon prior to addition of palladium on carbon (300 mg). The reaction mixture was stirred under hydrogen gas for 6 hours. The reaction mixture was filtered through Celite™ and the filtrate concentrated in vacuo to give a solid. The solid was triturated with hexane to afford the title compound as a white solid (1.7 g, 77%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite™
  2. washwashed with tetrahydrofuran
  3. concentrationThe resulting filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (26 mL)
  5. customdegassed with argon
  6. additionto addition of palladium on carbon (300 mg)
  7. stirringThe reaction mixture was stirred under hydrogen gas for 6 hours
  8. filtrationThe reaction mixture was filtered through Celite™
  9. concentrationthe filtrate concentrated in vacuo
  10. customto give a solid
  11. customThe solid was triturated with hexane

Sources & evidence

ORD record
ord-8c444c7801cb443fa09525ae103b2f10
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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