Triethylamine → 1-(3-Fluorophenyl)-5-iodo-1H-pyrazol-3-ylamine

HRID 83499Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 83499
CC1[N:3]([C:8]2[CH:12]=[C:11]([I:13])[N:10]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=3)[N:9]=2)C(C)=CC=1.[Cl-].O[NH3+].C(N(CC)CC)C>CCCCCC.C(OCC)(=O)C>[F:20][C:16]1[CH:15]=[C:14]([N:10]2[C:11]([I:13])=[CH:12][C:8]([NH2:3])=[N:9]2)[CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 21645Hydroxylamine HClHCID 866803553-(2,5-dimethylpyrrol-1-yl)-1-(3-fluorophenyl)-5-iodo-1H-pyrazole

Produkt 1

HCID 866803541-(3-Fluorophenyl)-5-iodo-1H-pyrazol-3-ylamineAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226206Ethyl acetate hexaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To a solution of 3-(2,5-dimethylpyrrol-1-yl)-1-(3-fluorophenyl)-5-iodo-1H-pyrazole (4.5 g) in ethanol/water (2/1, 81 ml) were sequentially added hydroxylammonium chloride (16.3 g) and triethylamine (3.3 ml), and the mixture was stirred at 95° C. for 17 hours. This reaction mixture was cooled to room temperature and concentrated under reduced pressure. To the resulting residue was added an 8M aqueous solution of sodium hydroxide, and the mixture was extracted with ethyl acetate. This organic layer was sequentially washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1) to give the titled compound (3.2 g).

Aufarbeitung

  1. temperatureThis reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionTo the resulting residue was added an 8M aqueous solution of sodium hydroxide
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThis organic layer was sequentially washed with water
  6. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1)

Quellen und Nachweise

ORD-Eintrag
ord-4958583d39724c58a3f05e282281cb19
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846746B2

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