4,4,4-Trifluoro-1-(1-cyclohexenyl)-1,3-butanedione → 2-[5-(1-Cyclohexenyl)-3-trifluoromethyl-pyrazol-1-yl]-5-methanesulfonyl-pyridine

HRID 1860589Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1860589
Cl.[NH:2]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:6][N:5]=1)[NH2:3].[F:14][C:15]([F:28])([F:27])[C:16](=O)[CH2:17][C:18]([C:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]=1)=O>C(O)C>[C:20]1([C:18]2[N:2]([C:4]3[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[O:11])=[O:12])=[CH:6][N:5]=3)[N:3]=[C:16]([C:15]([F:14])([F:27])[F:28])[CH:17]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]=1

Komponenten

4

Edukt 2

HCID 186240894,4,4-Trifluoro-1-(1-cyclohexenyl)-1,3-butanedioneHCID 222268132-Hydrazino-5-(methylsulfonyl)pyridine hydrochloride

Produkt 1

HCID 186240932-[5-(1-Cyclohexenyl)-3-trifluoromethyl-pyrazol-1-yl]-5-methanesulfonyl-pyridineAusbeute 18,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Hydrazino-5-(methylsulfonyl)pyridine hydrochloride (128 mg, 0.54 mmol) and 4,4,4-trifluoro-1-(1-cyclohexenyl)-1,3-butanedione (100 mg, 0.45 mmol) were mixed in ethanol (8 ml). The resulting reaction mixture was heated at reflux temperature for 35 hours. The solvent was then removed in vacuo, and the residue was partitioned between EtOAc and water. The organic layer was washed with brine and concentrated in vacuo. The product was purified by flash chromatography using methylene chloride to give the title compound (30.6 mg, 18%).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux temperature for 35 hours
  4. customThe solvent was then removed in vacuo
  5. customthe residue was partitioned between EtOAc and water
  6. washThe organic layer was washed with brine
  7. concentrationconcentrated in vacuo
  8. customThe product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-38d1ff26751b420a8f76418c60340e21
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06531492B1

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