Water → 7-Ethenyl-1H-indole

HRID 557168

Reaktionsgleichung

Reaktionsgleichung von HRID 557168
[CH2:1]([Sn](CCCC)(CCCC)C=C)[CH2:2]CC.[Cl-].[Li+].Br[C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:27]=1[NH:26][CH:25]=[CH:24]2.O>CN(C)C=O.C1([Pd-2](Cl)(Cl)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>[CH:1]([C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:27]=1[NH:26][CH:25]=[CH:24]2)=[CH2:2]

Komponenten

9

Edukt 4

HCID 962WaterHCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 27570207-Bromoindole

Produkt 1

HCID 145674047-Ethenyl-1H-indoleAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11776TriphenylphosphineKatalysatorHCID 178479785HCID 178479785, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Add tributyl(vinyl)tin (9.8 mL, 33.7 mmol), triphenyl-phosphine (0.4 g, 1.53 mmol), diphenylpalladium(II) dichloride (1.07 g, 1.53 mmol) and lithium chloride (4.0 g, 94.4 mmol) to 7-bromo-1H-indole (6.0 g, 30.6 mmol) in 150 mL of dimethylformamide and heat the resulting mixture at 100° C. overnight. Cool the reaction mixture to 20-24° C. and poured into a mixture of 150 mL of water and 150 mL of ethyl acetate. Wash the aqueous layer with additional ethyl acetate (3×100 mL), combine the organic layers, wash with saturated aqueous sodium chloride, dry over magnesium sulfate, filter, and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 5-10% ethyl acetate in hexanes. Combine fractions containing product and concentrate them under reduced pressure to provide the desired compound as a clear oil (3.5 g, 80%).

Aufarbeitung

  1. temperatureCool the reaction mixture to 20-24° C.
  2. washWash the aqueous layer with additional ethyl acetate (3×100 mL)
  3. washwash with saturated aqueous sodium chloride
  4. dry with materialdry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. washeluting with 5-10% ethyl acetate in hexanes
  8. additionCombine fractions containing product
  9. concentrationconcentrate them under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-968e909d4d174403abf46155922e6b3a
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058425B2

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