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Cesium carbonate → 3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methylsulfanyl-[2,2']bipyridine

HRID 228804
ノート
印刷プレビュー

反応式

HRID 228804 の反応式
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[C:6]([OH:15])=[CH:5][CH:4]=1.Cl[C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C1C=CN=CC=1.O>[CH3:28][O:27][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][C:23]=1[O:29][CH3:30])[N:20]=[CH:19][CH:18]=[C:17]2[O:15][C:6]1[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[N:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 1363851056-Methylsulfanyl-[2,2']bipyridin-3-ol

生成物 1

HCID 577565043-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methylsulfanyl-[2,2']bipyridine収率 9%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒
HCID 962
Water
溶媒

反応条件

温度
140 °C

実験手順

6-Methylsulfanyl-[2,2′]bipyridin-3-ol (6 mg), 4-chloro-6,7-dimethoxyquinoline (18 mg), 4-dimethylaminopyridine (10 mg), and cesium carbonate (27 mg) were suspended in N,N-dimethyl sulfoxide (1 ml), and the suspension was stirred at 140° C. overnight. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using acetone-hexane to give the title compound (1 mg, yield 8%).

後処理

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water and saturated brine
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by thin layer chromatography

出典と根拠

ORDレコード
ord-0a31084966c54a4c8af0a3455c60054b
出典データセット
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07560558B2

反応ノート

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