4,4,4-Trifluoro-1-(3-methyl-4-methoxylphenyl)-1,3-butanedione → 5-Methanesulfonyl-2-[5-(4-methoxy-3-methyl-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-pyridine

HRID 1860587Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1860587
[F:1][C:2]([F:18])([F:17])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([CH3:15])[CH:8]=1)=O.Cl.[NH:20]([C:22]1[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][N:23]=1)[NH2:21]>C(O)C>[CH3:15][C:9]1[CH:8]=[C:7]([C:5]2[N:20]([C:22]3[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][N:23]=3)[N:21]=[C:3]([C:2]([F:18])([F:17])[F:1])[CH:4]=2)[CH:12]=[CH:11][C:10]=1[O:13][CH3:14]

Komponenten

4

Edukt 2

HCID 113912984,4,4-Trifluoro-1-(3-methyl-4-methoxylphenyl)-1,3-butanedioneHCID 222268132-Hydrazino-5-(methylsulfonyl)pyridine hydrochloride

Produkt 1

HCID 129727295-Methanesulfonyl-2-[5-(4-methoxy-3-methyl-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-pyridineAusbeute 43,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4,4,4-Trifluoro-1-(3-methyl-4-methoxylphenyl)-1,3-butanedione (0.78 g, 3 mmol) and 2-hydrazino-5-(methylsulfonyl)pyridine hydrochloride (0.671 g, 3 mmol) were mixed in ethanol (60 ml), and the resulting reaction mixture was heated at reflux temperature for 72 hours. The reaction mixture was then cooled to room temperature, and the solvent was removed in vacuo. The residue was dissolved in EtOAc (250 ml), and the organic layer was washed with saturated NaHCO3 solution, brine, dried (MgSO4), and concentrated in vacuo. The residue was purified first by flash chromatography using 40% hexane in methylene chloride to and then by recrystallization from 3:1 of isooctane:methylene chloride to give the title compound (535 mg, 43%).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux temperature for 72 hours
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in EtOAc (250 ml)
  6. washthe organic layer was washed with saturated NaHCO3 solution, brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified first by flash chromatography
  10. customby recrystallization from 3:1 of isooctane

Quellen und Nachweise

ORD-Eintrag
ord-409230996d9342e8a538fcfe41357dc6
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06531492B1

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