Ethyl Acetate → 7-(2,4-Dichlorophenyl)-2-ethyl-3-nitropyrazolo[1,5-a]pyridine

HRID 9183

Reaktionsgleichung

Reaktionsgleichung von HRID 9183
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[N:15]=[C:16]([CH2:18][CH3:19])[CH:17]=[C:13]2[CH:12]=[CH:11][CH:10]=1.F[B-](F)(F)F.[O:25]=[N+:26]=[O:27].C(OCC)(=O)C>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[N:15]=[C:16]([CH2:18][CH3:19])[C:17]([N+:26]([O-:27])=[O:25])=[C:13]2[CH:12]=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 11073463Nitronium tetrafluoroborateHCID 219846357-(2,4-Dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridine

Produkt 1

HCID 219846667-(2,4-Dichlorophenyl)-2-ethyl-3-nitropyrazolo[1,5-a]pyridineAusbeute 35,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

After dissolving 7-(2,4-dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridine (280 mg) in acetonitrile (20 mL), nitronium tetrafluoroborate (255 mg) was added 4 times at 30 minute intervals while stirring on ice. The reaction mixture was added to ice water, extraction was performed with ethyl acetate and the extract was washed with water and brine. After drying over anhydrous magnesium sulfate and filtration, the solvent was concentrated under reduced pressure, the residue was purified by silica gel column chromatography, and the title compound (115 mg) was obtained from the n-hexane:ethyl acetate (20:1) fraction as yellow crystals.

Aufarbeitung

  1. additionwas added 4 times at 30 minute intervals
  2. washthe extract was washed with water and brine
  3. dry with materialAfter drying over anhydrous magnesium sulfate and filtration
  4. concentrationthe solvent was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b0d69462f11d46589ba57d6318c7fae0
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091215B2

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