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

HRID 638998

Reaktionsgleichung

Reaktionsgleichung von HRID 638998
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. 5b) (5.0 g, 16.23 mmole) in DME (80 mL) and H2O (40 mL) was added trivinyl boronate (1.96 g, 8.1 mmole), K2CO3 (2.23 g, 16.23 mmole) and Pd(PPh3)4 (0.19 g, 0.16 mmole). After 3 h at 90° C. under N2, the reaction solution was concentrated under vacuum and purified on silica (hexanes, EtOAc, 4:1) to give 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 (hexanes, EtOAc, 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-b581ffb8d7744a6690c3dfeef1a6f0bb
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691850B2

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