2-(Tributylstannyl)pyridine → 6-Methoxy-7-pyridin-2-yl-isoquinoline

HRID 228882ノート

反応式

HRID 228882 の反応式
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][C:3]=1[O:12][CH3:13].C([Sn](CCCC)(CCCC)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)CCC>CN(C)C=O.[Cu]=O>[CH3:13][O:12][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)[CH:9]=[N:8][CH:7]=[CH:6]2

参加物

5

反応物 2

HCID 6077842-(Tributylstannyl)pyridineHCID 230784917-Bromo-6-methoxyisoquinoline

生成物 1

HCID 230784766-Methoxy-7-pyridin-2-yl-isoquinoline収率 62%

試薬・触媒・溶媒 2

HCID 14829Copper oxide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

7-Bromo-6-methoxyisoquinoline (200 mg), tetrakistriphenylphosphine palladium(0) (97 mg), and copper(II) oxide (134 mg) were suspended in N,N-dimethylformamide (5 ml), tri-n-butyl-(2-pyridyl)-tin (618 mg) was added to the suspension, and the mixture was stirred at 100° C. overnight. The reaction solution was cooled to room temperature, the reaction solution was then fitlered, and the solvent was removed from the filtrate by distillation under the reduced pressure. Water was then added to the residue, and the mixture was extracted with dichloromethane. The dichloromethane layer was washed with water and saturated brine and was dried over anhydrous magnesium 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 6-methoxy-7-pyridin-2-yl-isoquinoline (122 mg, yield 62%).

後処理

  1. temperatureThe reaction solution was cooled to room temperature
  2. customthe solvent was removed from the filtrate by distillation under the reduced pressure
  3. additionWater was then added to the residue
  4. extractionthe mixture was extracted with dichloromethane
  5. washThe dichloromethane layer was washed with water and saturated brine
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under the reduced pressure
  8. customthe residue was purified by thin layer chromatography

出典と根拠

ORDレコード
ord-9d4d45675f394a7c8d07e929545bfc69
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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