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Piperidine → 5-(3-bromo-pyridin-5-yl)-1-(2,4-difluoro-phenyl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole

HRID 2207896
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2207896
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10](=O)[C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH:5]=[N:6][CH:7]=1.Cl.[F:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[NH:28][NH2:29].N1CCCCC1>C(O)C>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH:8]2[N:28]([C:22]3[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=3[F:20])[N:29]=[C:10]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH2:9]2)[CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 27333012,4-Difluorophenylhydrazine hydrochlorideHCID 1317359471-(5-Bromo-pyridin-3-yl)-4,4,5,5,5-pentafluoro-pent-1-en-3-one

Produkt 1

HCID 1184317135-(3-bromo-pyridin-5-yl)-1-(2,4-difluoro-phenyl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazoleAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

1-(5-Bromo-pyridin-3-yl)-4,4,5,5,5-pentafluoro-pent-1-en-3-one (2.9 g, 8.6 mmol) prepared in Step 3, 2,4-difluorophenylhydrazine hydrochloride (2.4 g, 8.6 mmol), and piperidine (1.7 mL, 17.3 mmol) were added to ethanol (86.4 mL). The reaction mixture was stirred at 90° C. for 18 hours, concentrated under reduced pressure, and then ethyl acetate was added thereto. The mixture was washed with distilled water, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/9) to give 2.4 g of the titled compound as a yellow solid.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. additionethyl acetate was added
  3. washThe mixture was washed with distilled water
  4. dry with materialdried on anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow liquid residue
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/9)

Quellen und Nachweise

ORD-Eintrag
ord-22398f6c30bb4cb8a5d1dd3bf73f2c5e
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09376420B2

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