3-Cyclopent-1-enyl-5-nitro-2-(2,2,2-trifluoro-ethoxy)-pyridine → 5-Cyclopentyl-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylamine

HRID 1253777Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1253777
[C:1]1([C:6]2[C:7]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[N:8][CH:9]=[C:10]([N+:12]([O-])=O)[CH:11]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1>C(OCC)(=O)C.[Pd]>[CH:1]1([C:6]2[CH:11]=[C:10]([NH2:12])[CH:9]=[N:8][C:7]=2[O:15][CH2:16][C:17]([F:18])([F:19])[F:20])[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

4

Edukt 1

HCID 712942943-Cyclopent-1-enyl-5-nitro-2-(2,2,2-trifluoro-ethoxy)-pyridine

Produkt 1

HCID 712941725-Cyclopentyl-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylamineAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-cyclopent-1-enyl-5-nitro-2-(2,2,2-trifluoro-ethoxy)-pyridine (Example 1b) (600 mg, 2.08 mmol) in ethyl acetate (30 mL) was added 10% Pd/C (554 mg, 0.52 mmol) under argon atmosphere. The reaction mixture was stirred under hydrogen balloon pressure for 12 h. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The crude thus obtained was purified by column chromatography (Combi-Flash, 40 g, 25% ethyl acetate/hexane) to get the title compound (375 mg, 69.16%) as colorless liquid; MS (ESI): 259 [M−H]−.

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude thus obtained
  4. customwas purified by column chromatography (Combi-Flash, 40 g, 25% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-39468a9e4dd149d5925ad3d06c84dc84
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455501B2

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