Potassium Carbonate → 6-Methoxy-7-pyridin-3-yl-isoquinoline

HRID 228885Notes

Reaction equation

HRID 228885 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].[N:14]1[CH:19]=[CH:18][CH:17]=[C:16](B(O)O)[CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:13][O:12][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[C:16]1[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=1)[CH:9]=[N:8][CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 230784917-Bromo-6-methoxyisoquinoline

Product 1

HCID 230783916-Methoxy-7-pyridin-3-yl-isoquinolineYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Bromo-6-methoxyisoquinoline (100 mg), tetrakistriphenylphosphine palladium(0) (49 mg), and 3-pyridineboronic acid (155 mg) were suspended in a mixed solvent composed of N,N-dimethylformamide (1.5 ml) and a 2 N aqueous potassium carbonate solution (1.5 ml), and the mixture was stirred at 80° C. for 4.5 hr. The reaction was cooled to room temperature, the reaction solution was then filtered, 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-3-yl-isoquinoline (42 mg, yield 85%).

Workup

  1. filtrationthe reaction solution was then filtered
  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-30362e69a1d1477ab8756999e0431f15
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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