4-[2-(5-Chloro-4-methyl-thiophen-2-yl)-quinolin-3-yloxy]-6,7-dimethoxy-quinoline → 6,7-Dimethoxy-4-[2-(3-methyl-butyl)-quinolin-3-yloxy]-quinoline

HRID 229064Notes

Reaction equation

HRID 229064 reaction equation
Cl[C:2]1S[C:5]([C:7]2[C:16]([O:17][C:18]3[C:27]4[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=4)[N:21]=[CH:20][CH:19]=3)=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)=[CH:4][C:3]=1[CH3:32]>C(N(CC)CC)C.CN(C)C=O.[OH-].[Pd+2].[OH-]>[CH3:29][O:28][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][C:24]=1[O:30][CH3:31])[N:21]=[CH:20][CH:19]=[C:18]2[O:17][C:16]1[C:7]([CH2:5][CH2:4][CH:3]([CH3:32])[CH3:2])=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

4

Reactant 1

HCID 577563924-[2-(5-Chloro-4-methyl-thiophen-2-yl)-quinolin-3-yloxy]-6,7-dimethoxy-quinoline2×

Product 1

HCID 577563906,7-Dimethoxy-4-[2-(3-methyl-butyl)-quinolin-3-yloxy]-quinolineYield 59.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 22056947triethylamine N,N-dimethylformamideSolvent

Procedure

4-[2-(5-Chloro-4-methyl-thiophen-2-yl)-quinolin-3-yloxy]-6,7-dimethoxy-quinoline (compound 290) (7 mg) was dissolved in triethylamine/N,N-dimethylformamide (0.5 ml/1.5 ml) to prepare a solution, 20% palladium hydroxide (68 mg) was added to the solution, and the mixture was stirred under a hydrogen gas atmosphere at room temperature overnight. The reaction solution was filtered, and the solvent was then removed by distillation under the reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then 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 thin layer chromatography using acetone-chloroform to give the title compound (3.6 mg, yield 56%).

Workup

  1. additionwas added to the solution
  2. filtrationThe reaction solution was filtered
  3. customthe solvent was then removed by distillation under the reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was then washed with water
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation under the reduced pressure
  9. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-53dee310287d4936949c56a1290529be
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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