Water → 3-(7-Benzyloxy-6-methoxy-quinolin-4-yloxy)-5,6,6'-trimethyl-[2,2']bipyridine

HRID 229067

反応式

HRID 229067 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([OH:16])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=2)=[N:6][C:7]=1[CH3:8].[CH2:17]([O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29](Cl)=[CH:30][CH:31]=[N:32]2)=[CH:27][C:26]=1[O:36][CH3:37])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C1C=CN=CC=1.CS(C)=O>[CH2:17]([O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29]([O:16][C:4]3[C:5]([C:9]4[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=4)=[N:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=3)=[CH:30][CH:31]=[N:32]2)=[CH:27][C:26]=1[O:36][CH3:37])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

参加物

7

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinolineHCID 1363851075,6-Dimethyl-2-(6-methylpyridin-2-yl)pyridin-3-ol

生成物 1

HCID 577565403-(7-Benzyloxy-6-methoxy-quinolin-4-yloxy)-5,6,6'-trimethyl-[2,2']bipyridine収率 72.2%

試薬・触媒・溶媒 2

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

反応条件

温度
130 °C

実験手順

5,6,6′-Trimethyl-[2,2′]bipyridin-3-ol (300 mg), 7-benzyloxy-4-chloro-6-methoxyquinoline (1.26 g), 4-dimethylaminopyridine (513 mg), and cesium carbonate (1.37 g) were suspended in dimethyl sulfoxide (6 ml), and the suspension was stirred at 130° C. overnight. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using chloroform-methanol to give the title compound (483 mg, yield 72%).

後処理

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionthe mixture was extracted with chloroform
  3. washThe chloroform layer was washed with saturated brine
  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 column chromatography

出典と根拠

ORDレコード
ord-146fedd606cf4b43b92bd93f65c0f8f9
出典データセット
uspto-grants-2009_07
特許番号
US07560558B2

関連ノート

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