Cesium carbonate → HCID 58547859, Verbindung

HRID 2207782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2207782
C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.[NH:18]1[CH2:21][CH:20]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:19]1>CN(C=O)C.O>[N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[CH:17][C:8]=1[N:18]1[CH2:21][CH:20]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH2:19]1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 119282-ChloroquinolineHCID 15194053-Aminoazetidine, 3-BOC protected

Produkt 1

HCID 58547859HCID 58547859, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of Cs2CO3 (3.2 g, 10.0 mmol), 2-chloro-quinoline (0.8 g, 5.0 mmol) and tert-butyl azetidin-3-ylcarbamate (0.8 g, 5.0 mmol) was dissolved in DMF (20 mL) and the resulting mixture was heated to 100° C. overnight. Then the mixture was diluted with water (20 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were combined and washed with water (20 mL) and brine (20 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (20% to 70% EtOAc in petroleum ether) to give tert-butyl (1-(quinolin-2-yl)azetidin-3-yl)carbamate (0.8 g, 2.9 mmol, 53% yield) as white solid. ESI-MS (M+1): 300 calc. for C17H21N3O2 299.

Aufarbeitung

  1. extractionextracted with EtOAc (2×50 mL)
  2. washwashed with water (20 mL) and brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by flash column chromatography on silica gel (20% to 70% EtOAc in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-56465888ccc04052a8b622e476702890
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376450B2

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