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

HRID 229056노트

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HRID 229056 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
140 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-445e422ad73a45c0842593b7dbbf6241
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

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