Cesium carbonate → 3-(6,7-Dimethoxy-quinolin-4-yloxy)-5,6,5'-trimethyl-[2,2']bipyridine

HRID 228824ノート

反応式

HRID 228824 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([OH:16])[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][N:10]=2)=[N:6][C:7]=1[CH3:8].Cl[C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F-].[Cs+]>CN(C1C=CN=CC=1)C.O.CS(C)=O>[CH3:29][O:28][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][C:24]=1[O:30][CH3:31])[N:21]=[CH:20][CH:19]=[C:18]2[O:16][C:4]1[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][N:10]=2)=[N:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=1

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 25953Cesium fluorideHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 1363851085,6,5'-Trimethyl-[2,2']bipyridin-3-ol

生成物 1

HCID 577564513-(6,7-Dimethoxy-quinolin-4-yloxy)-5,6,5'-trimethyl-[2,2']bipyridine収率 29.4%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
140 °C

実験手順

Dimethyl sulfoxide (2.8 ml) was added to 5,6,5′-trimethyl-[2,2′]bipyridin-3-ol (60 mg), 4-chloro-6,7-dimethoxyquinoline (184 mg), cesium carbonate (274 mg), 4-(N,N-dimethylamino)-pyridine (51 mg), and cesium fluoride (64 mg) to prepare a solution which was then 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 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 (33 mg, yield 29%).

後処理

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

出典と根拠

ORDレコード
ord-2d83b5505904495294df572729fa61b7
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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