1,2-Dimethoxyethane → 8-Ethenyl-2-methoxy-1,5-naphthyridine

HRID 2356313

Reaktionsgleichung

Reaktionsgleichung von HRID 2356313
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[N:15]=2)[N:10]=[CH:9][CH:8]=1)(=O)=O.C([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[CH:8]=[CH:9][N:10]=[C:11]2[C:16]=1[N:15]=[C:14]([O:17][CH3:18])[CH:13]=[CH:12]2)=[CH2:30]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 575995738-Ethenyl-2-methoxy-1,5-naphthyridineAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 6-(methyloxy)-1,5-naphthyridin-4-yl trifluoromethanesulfonate (from Prep. 2b) (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) 187 (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-4dc59aec98ca4d6e96df73ff9cc3d64b
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759340B2

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