Dimethyl Sulfoxide → 3-(7-Chloroquinolin-4-yloxy)-5,6,5'-trimethyl-[2,2']-bipyridine

HRID 229056ノート

反応式

HRID 229056 の反応式
CS(C)=O.[CH3:5][C:6]1[CH:7]=[C:8]([OH:20])[C:9]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=2)=[N:10][C:11]=1[CH3:12].Cl[C:22]1[C:31]2[C:26](=[CH:27][C:28]([Cl:32])=[CH:29][CH:30]=2)[N:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O>[Cl:32][C:28]1[CH:27]=[C:26]2[C:31]([C:22]([O:20][C:8]3[C:9]([C:13]4[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=4)=[N:10][C:11]([CH3:12])=[C:6]([CH3:5])[CH:7]=3)=[CH:23][CH:24]=[N:25]2)=[CH:30][CH:29]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 68664,7-DichloroquinolineHCID 10796Cesium carbonateHCID 1363851085,6,5'-Trimethyl-[2,2']bipyridin-3-ol

生成物 1

HCID 577565993-(7-Chloroquinolin-4-yloxy)-5,6,5'-trimethyl-[2,2']-bipyridine収率 94%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
140 °C

実験手順

Dimethyl sulfoxide (2 ml) was added to 5,6,5′-trimethyl-[2,2′]bipyridin-3-ol (50 mg), 4,7-dichloroquinoline (139 mg), and cesium carbonate (228 mg), and the mixture was stirred at 140° C. for 5 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 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 chloroform-methanol to give the title compound (77 mg, yield 94%).

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 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-445e422ad73a45c0842593b7dbbf6241
出典データセット
uspto-grants-2009_07
特許番号
US07560558B2

反応ノート

読み込み中…