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

HRID 638998

反応式

HRID 638998 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 575995738-Ethenyl-2-methoxy-1,5-naphthyridine収率 81%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-b581ffb8d7744a6690c3dfeef1a6f0bb
出典データセット
uspto-grants-2010_04
特許番号
US07691850B2

関連ノート

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