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

HRID 1261771Notes

Reaction equation

HRID 1261771 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12](=[O:26])[C:13]2[C:14]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:15][CH:16]=[CH:17][CH:18]=2)=[C:6]([F:27])[CH:5]=1.[H][H]>CO.C(OCC)(=O)C.[Pt](=O)=O>[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12](=[O:26])[C:13]2[C:14]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:15][CH:16]=[CH:17][CH:18]=2)=[C:6]([F:27])[CH:5]=1

Participants

6

Reactant 2

HCID 866720543-fluoro-4-[(E)-3-oxo-3-(2-phenylamino-pyridin-3-yl)-propenyl]-benzoic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 708169163-Fluoro-4-[3-oxo-3-(2-phenylamino-pyridin-3-yl)-propyl]-benzoic acid methyl esterYield 96.3%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-fluoro-4-[(E)-3-oxo-3-(2-phenylamino-pyridin-3-yl)-propenyl]-benzoic acid methyl ester (890 mg, 2.36 mmol) in methanol (59.1 mL) and ethyl acetate (59.1 mL) at 25° C. was treated with platinum(IV) oxide (26.8 mg, 118 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 3-fluoro-4-[3-oxo-3-(2-phenylamino-pyridin-3-yl)-propyl]-benzoic acid methyl ester (860 mg, 96.2%) as a dark green 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-2f46f9dca4f943f5b73eb4778e7649e8
Source dataset
uspto-grants-2013_06
Patent number
US08471027B2

Reaction notes

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