5-Bromoindole → (E)-5-(2-(phenylsulfonyl)vinyl)-1H-indole

HRID 473055

Reaktionsgleichung

Reaktionsgleichung von HRID 473055
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[C:11]1([S:17]([CH:20]=[CH2:21])(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CCN(C(C)C)C(C)C>C(#N)C.ClCCl.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:11]1([S:17](/[CH:20]=[CH:21]/[C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

8

Edukt 4

HCID 249055-BromoindoleHCID 79664Phenyl vinyl sulfoneHCID 80271Tri-o-tolylphosphineHCID 81531Diisopropylethylamine

Produkt 1

HCID 15521560(E)-5-(2-(phenylsulfonyl)vinyl)-1H-indoleAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 5-bromoindole (5.0 g, 25.5 mmol), phenylvinylsulfone (7.50 g, 44.64 mmol), Pd(OAc)2 (0.46 g, 2.05 mmol), tri-O-tolylphosphine (1.55 g, 5.10 mmol) and DIPEA (3.6 g) was heated to reflux for 18 h in acetonitrile. The reaction mixture was cooled to RT, diluted with dichloromethane and filtered over a bed of filter aid. The solvent is completely distilled off and to the crude fresh dichloromethane was charged. The filtrate was sequentially washed with water and brine, and dried over sodium sulphate. The organic layer was concentrated under vacuum and the product precipitated from ethylacetate and hexane as a solid in about 65-70% yield.

Aufarbeitung

  1. filtrationfiltered over a bed of filter aid
  2. distillationThe solvent is completely distilled off and to the crude fresh dichloromethane
  3. additionwas charged
  4. washThe filtrate was sequentially washed with water and brine
  5. dry with materialdried over sodium sulphate
  6. concentrationThe organic layer was concentrated under vacuum
  7. customthe product precipitated from ethylacetate and hexane as a solid in about 65-70% yield

Quellen und Nachweise

ORD-Eintrag
ord-9381a37328dc44ff90162a3771f26bff
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633239B2

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