Potassium Carbonate → Tert-butyl 8-(3-chloro-2-pyridinyl)-3,8-diazabicyclo[3.2.1]octane-3-carboxylate

HRID 1246709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1246709
[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:2]2.Br[C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][N:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[Cl:23][C:22]1[C:17]([N:8]2[CH:5]3[CH2:6][CH2:7][CH:1]2[CH2:2][N:3]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]3)=[N:18][CH:19]=[CH:20][CH:21]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 70163262-Bromo-3-chloropyridineHCID 21904757tert-Butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate

Produkt 1

HCID 21904766Tert-butyl 8-(3-chloro-2-pyridinyl)-3,8-diazabicyclo[3.2.1]octane-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

tert-Butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate (454 mg, 2.36 mmol) and 2-bromo-3-chloropyridine (418 mg, 1.97 mmol) were combined in dry N,N-dimethylformamide (10 mL) and treated with potassium carbonate (408 mg, 2.95 mmol). After stirring at 120° C. for 48 hours, the mixture was allowed to cool to room temperature, diluted with ethyl acetate, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (4:1, hexanes:ethyl acetate) to provide the title compound.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by chromatography on silica gel (4:1, hexanes:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-fdd14dc580784d4989095ee35bd292ea
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129235B2

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