Water → 4-(5-Chloro-2-cyclopentyloxy-pyridin-3-yloxy)-6,7-dimethoxy-quinoline

HRID 228759Notes

Reaction equation

HRID 228759 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[C:5]([OH:8])=[N:6][CH:7]=1.[CH:24]1(Br)[CH2:28][CH2:27][CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[C:5]([O:8][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 1784868084-(5-Chloro-2-hydroxy-pyridin-3-yloxy)-6,7-dimethoxyquinoline

Product 1

HCID 230784064-(5-Chloro-2-cyclopentyloxy-pyridin-3-yloxy)-6,7-dimethoxy-quinolineYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(5-Chloro-2-hydroxy-pyridin-3-yloxy)-6,7-dimethoxyquinoline (39 mg) was suspended in N,N-dimethylformamide (7 ml). Cyclopentyl bromide (0.3 ml) and potassium carbonate (300 mg) were added to the suspension, and the mixture was stirred at room temperature for 2 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous sodium hydrogencarbonate solution and 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 (29 mg, yield 62%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous sodium hydrogencarbonate solution and water
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d6516d28e80f43e291a2e572673659f7
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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