1,2-Dimethoxyethane → 6-Methoxy-4-vinyl-quinoline

HRID 639006

Reaktionsgleichung

Reaktionsgleichung von HRID 639006
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])N=2)[N:10]=[CH:9][CH:8]=1)(=O)=O.[C:21]([O-])([O-])=O.[K+].[K+].CO[CH2:29][CH2:30]OC>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:29]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:21]=2)[N:10]=[CH:9][CH:8]=1)=[CH2:30]

Komponenten

6

Edukt 3

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 112552656-Methoxy-1,5-naphthyridin-4-yl trifluoromethanesulfonate

Produkt 1

HCID 590262186-Methoxy-4-vinyl-quinolineAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 6-(methyloxy)-1,5-naphthyridin-4-yl trifluoromethanesulfonate (5.0 g, 16.23 mmol) in DME (80 mL) and H2O (40 mL) was added trivinyl boronate (1.96 g, 8.1 mmol), K2CO3 (2.23 g, 16.23 mmol) and Pd(PPh3)4 (0.19 g, 0.16 mmol). After 3 h at 90° C. under N2, the reaction solution was concentrated under vacuum and purified on silica (hexane/EtOAc, 4:1) to give the title compound as a yellow oil (2.44 g, 81%): LC/MS (m/z) (ES) 186 (M+H)+.

Aufarbeitung

  1. concentrationthe reaction solution was concentrated under vacuum
  2. custompurified on silica (hexane/EtOAc, 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-7439aa1200dc4475801e0bcb450a3233
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691850B2

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