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

HRID 473054

Reaktionsgleichung

Reaktionsgleichung von HRID 473054
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.C(N(CC)CC)C>CN(C=O)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 8471TriethylamineHCID 249055-BromoindoleHCID 79664Phenyl vinyl sulfoneHCID 80271Tri-o-tolylphosphine

Produkt 1

HCID 15521560(E)-5-(2-(phenylsulfonyl)vinyl)-1H-indoleAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 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 triethylamine (4.88 g, 48.46 mmol) was heated to 95-105° C. for 6-15 h in DMF. The reaction mixture was cooled to RT, diluted with dichloromethane and filtered over a bed of filter aid. 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 dichloromethane and hexane as a solid in about 85-90% yield.

Aufarbeitung

  1. filtrationfiltered over a bed of filter aid
  2. washThe filtrate was sequentially washed with water and brine
  3. dry with materialdried over sodium sulphate
  4. concentrationThe organic layer was concentrated under vacuum
  5. customthe product precipitated from dichloromethane and hexane as a solid in about 85-90% yield

Quellen und Nachweise

ORD-Eintrag
ord-6becbcf7f69841c2875688099706b4fb
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633239B2

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