4-[(E)-3-oxo-3-(2-phenylamino-6-trifluoromethyl-pyridin-3-yl)-propenyl]-benzoic acid methyl ester → 4-[3-Oxo-3-(2-phenylamino-6-trifluoromethyl-pyridin-3-yl)-propyl]-benzoic acid methyl ester

HRID 1261776Notes

Reaction equation

HRID 1261776 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12](=[O:30])[C:13]2[C:14]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=2)=[CH:6][CH:5]=1.[H][H]>CC(C)=O.[Pd]>[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12](=[O:30])[C:13]2[C:14]([NH:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[N:15][C:16]([C:19]([F:21])([F:22])[F:20])=[CH:17][CH:18]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 866720564-[(E)-3-oxo-3-(2-phenylamino-6-trifluoromethyl-pyridin-3-yl)-propenyl]-benzoic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 708172854-[3-Oxo-3-(2-phenylamino-6-trifluoromethyl-pyridin-3-yl)-propyl]-benzoic acid methyl esterYield 65.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 180AcetoneSolvent

Procedure

A solution of 4-[(E)-3-oxo-3-(2-phenylamino-6-trifluoromethyl-pyridin-3-yl)-propenyl]-benzoic acid methyl ester (4.02 g, 9.43 mmol) in acetone (150 mL) at 25° C. was treated with 10% palladium on activated carbon (402 mg, 3.78 μmol). The reaction was stirred under a balloon of hydrogen gas for 18 h. At this time, the reaction was filtered through a pad of Celite® and was rinsed with a solution of 10% methanol/methylene chloride (3×75 mL). The filtrate was concentrated in vacuo to afford 4-[3-oxo-3-(2-phenylamino-6-trifluoromethyl-pyridin-3-yl)-propyl]-benzoic acid methyl ester (2.64 g, 65.4%) as a yellow solid. The material was used without further purification.

Workup

  1. filtrationAt this time, the reaction was filtered through a pad of Celite®
  2. washwas rinsed with a solution of 10% methanol/methylene chloride (3×75 mL)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-46c9830399d4402486a38e4c9baee2d1
Source dataset
uspto-grants-2013_06
Patent number
US08471027B2

Reaction notes

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