Sodium Carbonate → (E)-3-[1-(4-Pyridin-3-ylphenylsulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester

HRID 870091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870091
[C:1]([O:5][C:6](=[O:24])/[CH:7]=[CH:8]/[C:9]1[CH:13]=[CH:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20](Br)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[N:25]1[CH:30]=[CH:29][CH:28]=[C:27](B(O)O)[CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd](Cl)Cl>[C:1]([O:5][C:6](=[O:24])/[CH:7]=[CH:8]/[C:9]1[CH:13]=[CH:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:27]3[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 66646304(E)-3-[1-(4-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester2×

Produkt 1

HCID 66646399(E)-3-[1-(4-Pyridin-3-ylphenylsulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 13169693Triphenylphosphine palladium dichlorideKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

0.18 g (E)-3-[1-(4-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester (compound D4) and 62 mg 3-pyridylboronic acid are dissolved in 10 ml DME. A catalytic amount of bis-(triphenylphosphin-palladium (II)-chloride and 0.6 ml of an aqueous solution of sodium carbonate are added and the mixture is heated to reflux temperature overnight. The title compound is isolated by means of chromatography.

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureto reflux temperature overnight

Quellen und Nachweise

ORD-Eintrag
ord-7a816234ffa940a7bfabdbefb800ca9a
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969401B2

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