Toluene → 2-[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-phenol

HRID 228763ノート

反応式

HRID 228763 の反応式
C1(C)C=CC=CC=1.C(=O)([O-])O.[Na+].I[C:14]1[C:19]([O:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=3)[N:24]=[CH:23][CH:22]=2)=[CH:18][CH:17]=[C:16]([CH3:35])[N:15]=1.[OH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1B(O)O>O>[CH3:32][O:31][C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][C:27]=1[O:33][CH3:34])[N:24]=[CH:23][CH:22]=[C:21]2[O:20][C:19]1[C:14]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[OH:36])=[N:15][C:16]([CH3:35])=[CH:17][CH:18]=1

参加物

6

反応物 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 2773454(2-Hydroxyphenyl)boronic acidHCID 100936734-[(2-Iodo-6-methyl-3-pyridyl)oxy]-6,7-dimethoxyquinoline2 回

生成物 1

HCID 1361316222-[3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methyl-pyridin-2-yl]-phenol収率 97.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

Toluene (1 ml) and a saturated aqueous sodium hydrogencarbonate solution (0.5 ml) were added to 4-(2-iodo-6-methyl-pyridin-3-yloxy)-6,7-dimethoxy-quinoline (compound 116) (50 mg), tetrakistriphenylphosphine palladium (14 mg), and 2-hydroxyphenylboronic acid (81 mg) under an argon atmosphere, and the mixture was stirred at 80° 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 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 (45 mg, yield 93%).

後処理

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionthe mixture was extracted with chloroform
  3. washThe chloroform layer was then 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-2ae60b2c3df847878384a383a9a2ad33
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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