Potassium Carbonate → 5-(4-Bromo-but-2-enyloxy)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

HRID 49493

Reaktionsgleichung

Reaktionsgleichung von HRID 49493
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[Br:24][CH:25]=[CH:26][CH2:27][CH2:28]Br>CN(C=O)C.CCOCC.O>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:28][CH:27]=[CH:26][CH2:25][Br:24])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 10657398N-Boc-5-HydroxyindolineHCID 536293111,4-Dibromobut-1-ene

Produkt 1

HCID 695150785-(4-Bromo-but-2-enyloxy)-2,3-dihydro-indole-1-carboxylic acid tert-butyl esterAusbeute 31,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

514 mg (2.3 mmol) 5-Hydroxy-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester in 12 ml DMF were treated with 830 mg (6 mmol) powdered K2CO3 and 1070 mg (5 mmol) 1,4-dibromobutene. The suspension was stirred at 50° C. for 3 h, cooled to RT, diluted with ether and water. The aqueous phase was extracted with ether, the organic phases were washed with water and dried over Na2SO4. Column chromatography on silica gel with hexane/EtOAc 9:1 yielded 270 mg (31%) 5-(4-Bromo-but-2-enyloxy)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester as colorless solid, MS: 368 (MH+, 1Br).

Aufarbeitung

  1. temperaturecooled to RT
  2. extractionThe aqueous phase was extracted with ether
  3. washthe organic phases were washed with water
  4. dry with materialdried over Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-191c59b28e964af6a3cd91ce94ab1f94
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706751B2

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