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Water → 7-Benzyloxy-4-[2-(4,5-dimethyl-thiazol-2-yl)-5,6-dimethyl-pyridin-3-yloxy]-6-methoxy-quinoline

HRID 229079
ノート
印刷プレビュー

反応式

HRID 229079 の反応式
[CH3:1][C:2]1[N:3]=[C:4]([C:8]2[C:13]([OH:14])=[CH:12][C:11]([CH3:15])=[C:10]([CH3:16])[N:9]=2)[S:5][C:6]=1[CH3:7].[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:14][C:13]3[C:8]([C:4]4[S:5][C:6]([CH3:7])=[C:2]([CH3:1])[N:3]=4)=[N:9][C:10]([CH3:16])=[C:11]([CH3:15])[CH:12]=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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinolineHCID 1358548345,6-Dimethyl-2-(4,5-dimethylthiazol-2-yl)pyridin-3-ol

生成物 1

HCID 230782777-Benzyloxy-4-[2-(4,5-dimethyl-thiazol-2-yl)-5,6-dimethyl-pyridin-3-yloxy]-6-methoxy-quinoline収率 22.1%

試薬・触媒・溶媒 2

HCID 14284
4-(Dimethylamino)pyridine
触媒
HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
130 °C

実験手順

2-(4,5-Dimethyl-thiazol-2-yl)-5,6-dimethyl-pyridin-3-ol (200 mg), 7-benzyloxy-4-chloro-6-methoxyquinoline (768 mg), 4-dimethylaminopyridine (313 mg), and cesium carbonate (313 mg) were suspended in dimethyl sulfoxide (4 ml), and the mixture was stirred at 130° C. for 9 hr. 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 (94 mg, yield 22%).

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-4e9cdda990034a4784060ead2a1ce582
出典データセット
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07560558B2

反応ノート

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