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

HRID 2356313노트

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HRID 2356313 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-4dc59aec98ca4d6e96df73ff9cc3d64b
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07759340B2

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