2-(2-Benzyloxy-pyridin-4-yl)-3-(2,4-dichloro-phenyl)-1,1,1-trifluoro-butan-2-ol → 4-[2-(2,4-Dichloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1H-pyridin-2-one

HRID 333774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 333774
C([O:8][C:9]1[CH:14]=[C:13]([C:15]([OH:30])([CH:20]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])[CH3:21])[C:16]([F:19])([F:18])[F:17])[CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1>C(OCC)(=O)C>[Cl:29][C:23]1[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:22]=1[CH:20]([CH3:21])[C:15]([C:13]1[CH:12]=[CH:11][NH:10][C:9](=[O:8])[CH:14]=1)([OH:30])[C:16]([F:19])([F:18])[F:17]

Komponenten

3

Edukt 1

HCID 252538282-(2-Benzyloxy-pyridin-4-yl)-3-(2,4-dichloro-phenyl)-1,1,1-trifluoro-butan-2-ol

Produkt 1

HCID 574212564-[2-(2,4-Dichloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1H-pyridin-2-oneAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-(2-Benzyloxy-pyridin-4-yl)-3-(2,4-dichloro-phenyl)-1,1,1-trifluoro-butan-2-ol (Example 54, 300 mg) was dissolved in ethyl acetate (10 mL) and the flask was flushed with argon. Palladium on activated charcoal (10% Pd, 75 mg) was added and the mixture was hydrogenated for 2 hours with vigorous stirring. The suspension was filtered and the catalyst was washed with methanol. The filtrate was concentrated in vacuo and the residue was dried in high vacuum to give the title compound as a light brown powder (217 mg). MS (m/e, ISP neg. ion): 364.4 (M−H+)−.

Aufarbeitung

  1. customthe flask was flushed with argon
  2. additionPalladium on activated charcoal (10% Pd, 75 mg) was added
  3. filtrationThe suspension was filtered
  4. washthe catalyst was washed with methanol
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was dried in high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ad17e4d85c25489b9b5bd949355b9385
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883786B2

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