Water → 4-(2-Cyclopentyloxy-pyridin-3-yloxy)-6,7-dimethoxy-quinoline

HRID 228738Notes

Reaction equation

HRID 228738 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:17]([OH:22])=[N:18][CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[CH:29]1(Br)[CH2:33][CH2:32][CH2:31][CH2:30]1.O>C(Cl)(Cl)Cl>[CH:29]1([O:22][C:17]2[C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 178486809HCID 178486809, compound

Product 1

HCID 230783854-(2-Cyclopentyloxy-pyridin-3-yloxy)-6,7-dimethoxy-quinolineYield 55%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6,7-Dimethoxy-4-(2-hydroxy-pyridin-3-yloxy)-quinoline (21 mg) was dissolved in chloroform (7 ml) to prepare a solution. Potassium carbonate (300 mg) and cyclopentyl bromide (0.2 ml) were added to the solution. The mixture was stirred at room temperature overnight, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was 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 column chromatography using acetone-chloroform to give the title compound (14 mg, yield 55%).

Workup

  1. customto prepare a solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was 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 column chromatography

Sources & evidence

ORD record
ord-e73a2fae1fa34805996adcfee01b8cde
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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