Cesium carbonate → 2-(Thiazol-2-yl)-2-aza-bicyclo[2.2.2]octan-3-one

HRID 2176936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2176936
[CH:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=[O:9])[NH:2]2.Br[C:11]1[S:12][CH:13]=[CH:14][N:15]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[S:12]1[CH:13]=[CH:14][N:15]=[C:11]1[N:2]1[C:3](=[O:9])[CH:4]2[CH2:7][CH2:8][CH:1]1[CH2:6][CH2:5]2

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 764302-BromothiazoleHCID 1378872-Azabicyclo(2.2.2)octan-3-oneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Produkt 1

HCID 673832052-(Thiazol-2-yl)-2-aza-bicyclo[2.2.2]octan-3-oneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

A mixture of 2-azabicyclo[2.2.2]octan-3-one (0.5 g, 4.0 mmol), 2-bromothiazole (0.79 g, 4.81 mmol), Cs2CO3 (2.0 g, 6.0 mmol), xantphos (0.19 g, 0.32 mmol) and 1,4-dioxane (25 ml) was degassed with argon gas for 15 min. Tetrakis(triphenylphosphine)palladium (0) (0.18 g, 0.16 mmol) was added, degassed for another 15 min and stirred at 125° C. for 3 h in a sealed tube. After cooling to room temperature the reaction mixture was filtered and the filtrate was evaporated under reduced pressure to afford the crude compound. Purification by column chromatography over neutral alumina using 10% ethyl acetate in petroleum ether as eluent afford 500 mg (60%) of 2-(thiazol-2-yl)-2-aza-bicyclo[2.2.2]octan-3-one as pale yellow solid.

Aufarbeitung

  1. customwas degassed with argon gas for 15 min
  2. customdegassed for another 15 min
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. filtrationwas filtered
  5. customthe filtrate was evaporated under reduced pressure
  6. customto afford the crude compound
  7. customPurification by column chromatography over neutral alumina using 10% ethyl acetate in petroleum ether as eluent

Quellen und Nachweise

ORD-Eintrag
ord-020ad6c0294345018cb2ddf97bc1271b
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067888B2

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