HCID 58256801, compound → HCID 58948772, compound

HRID 1013045Notes

Reaction equation

HRID 1013045 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]([CH3:20])=[C:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[C:17]([CH3:29])=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.O1CCCC1.[Pd]>[CH3:28][O:27][C:24]1[CH:23]=[CH:22][C:21]([C:18]2[C:17]([CH3:29])=[N:16][N:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)[C:19]=2[CH3:20])=[CH:26][CH:25]=1

Participants

5

Reactant 1

HCID 58256801HCID 58256801, compound

Product 1

HCID 58948772HCID 58948772, compoundYield 83.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(4-benzyloxyphenyl)-4-(4-methoxyphenyl)-3,5-dimethyl-1H-pyrazole (57 mg, 0.15 mmol) in methanol (2 mL) and tetrahydrofuran (3 mL) was flushed with nitrogen. A catalytic amount of palladium on carbon (10% wet) was added, and the reaction was again flushed with nitrogen followed by hydrogen. After the reaction was allowed to stir at room temperature for 1 hour, it was filtered through a pad of Celite and concentrated to give 37 mg of the desired phenol. LC-MS (C18H18N2O2 calculated 294) m/z 295 (M+H).

Workup

  1. customthe reaction was again flushed with nitrogen
  2. filtrationit was filtered through a pad of Celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0e7d7725e0dd4b328c696f3020a6202c
Source dataset
uspto-grants-2011_07
Patent number
US07981896B2

Reaction notes

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