5-[(E)-2-phenylvinyl]-3-[4-(trifluoromethyl)phenyl]-1H-pyrazole → 5-(2-phenylethyl)-3-[4-(trifluoromethyl)phenyl]-1H-pyrazole

HRID 2110855Notes

Reaction equation

HRID 2110855 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9]2[NH:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O1CCCC1.C(O)C.[C].[Pd]>[C:1]1([CH2:7][CH2:8][C:9]2[NH:13][N:12]=[C:11]([C:14]3[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=3)[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 1

HCID 231599615-[(E)-2-phenylvinyl]-3-[4-(trifluoromethyl)phenyl]-1H-pyrazole

Product 1

HCID 231573735-(2-phenylethyl)-3-[4-(trifluoromethyl)phenyl]-1H-pyrazoleYield 56.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-[(E)-2-Phenylvinyl]-3-[4-(trifluoromethyl)phenyl]-1H-pyrazole (1.56 g, 4.96 mmol) was dissolved in a mixed solvent of tetrahydrofuran (30 mL) and ethanol (30 mL), 10% palladium-carbon (50% water-containing product, 500 mg) was added, and the mixture was stirred at room temperature under an atmospheric hydrogen atmosphere for 2 hr. The catalyst was filtered off and the filtrate was concentrated to give the title compound (880 mg, yield 56%) as colorless crystals. MS: m/z 317 (MH+).

Workup

  1. additionwas added
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-bd6a9122af7c4ec688894b2aa6c9fcf3
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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