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

HRID 228882Notes

Reaction equation

HRID 228882 reaction equation
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

Participants

5

Reactant 2

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

Product 1

HCID 230784766-Methoxy-7-pyridin-2-yl-isoquinolineYield 62%

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-9d4d45675f394a7c8d07e929545bfc69
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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