Dimethyl Sulfoxide → 3-(6,7-Dimethoxy-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine

HRID 228813ノート

反応式

HRID 228813 の反応式
CS(C)=O.[CH3:5][C:6]1[CH:7]=[C:8]([OH:19])[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[N:10][C:11]=1[CH3:12].Cl[C:21]1[C:30]2[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=2)[N:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O>[CH3:32][O:31][C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][C:27]=1[O:33][CH3:34])[N:24]=[CH:23][CH:22]=[C:21]2[O:19][C:8]1[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[N:10][C:11]([CH3:12])=[C:6]([CH3:5])[CH:7]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 1356000565,6-Dimethyl-2-pyridin-2-yl-pyridin-3-ol

生成物 1

HCID 577565303-(6,7-Dimethoxy-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine収率 20.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
130 °C

実験手順

Dimethyl sulfoxide (1.5 ml) was added to 5,6-dimethyl-[2,2′]-bipyridin-3-ol (30 mg), 4-chloro-6,7-dimethoxyquinoline (101 mg), and cesium carbonate (147 mg), and the mixture was stirred at 130° C. for 7 hr. 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 was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using hexane-acetone to give the title compound (12 mg, yield 20%).

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
  4. dry with materialwas dried over anhydrous sodium 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-0677c276e7c84ebfa6ab15463b16ce40
出典データセット
uspto-grants-2009_07
特許番号
US07560558B2

反応ノート

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