1,3-Dibromopropane → Indole-bromide

HRID 966496

Reaktionsgleichung

Reaktionsgleichung von HRID 966496
C[C:2]1[NH:3][C:4]2[C:9]([C:10]=1C(OCC1C=CC=CC=1)=O)=[CH:8][C:7](O)=[CH:6][CH:5]=2.C([O-])([O-])=O.[Cs+].[Cs+].[Br:28]CCCBr>C(#N)C>[Br-:28].[NH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:2]1

Komponenten

5

Edukt 3

HCID 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 109239755-Hydroxy-2-methyl-1H-indole-3-carboxylic acid benzyl ester

Produkt 1

HCID 22381015Indole-bromideAusbeute 62,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-Methyl-3-benzyloxycarbonyl-5-hydroxyindole (0.558 g, 1.980 mmol, 1 eq) was suspended in acetonitrile (10 mL) under Ar. Cs2CO3 (0.645 g, 1.980 mmol, 1 eq) and KI (0.328 g, 1.980 mmol, 1 eq) were added followed by 1,3-dibromopropane (0.523 g, 2.590 mmol, 1.3 eq). The reaction mixture was stirred and heated to reflux for 20 hours. Then the reaction was quenched with saturated sodium bicarbonate and extracted with ethyl acetate (3×). The combined organic phases were washed with brine and dried over Na2SO4. After removing the solvent, the residue was loaded on silica gel and chromatographed, eluting with ethyl acetate/hexane (1/5). 0.244 g (31%) of the indole-bromide was obtained as a colorless oil.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 20 hours
  3. customThen the reaction was quenched with saturated sodium bicarbonate
  4. extractionextracted with ethyl acetate (3×)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over Na2SO4
  7. customAfter removing the solvent
  8. customchromatographed
  9. washeluting with ethyl acetate/hexane (1/5)

Quellen und Nachweise

ORD-Eintrag
ord-c2545d97712146679bf4225d98bdc00b
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06951848B2

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