Phenylboronic Acid → N-[2-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methylphenyl]-N-phenylamine

HRID 228522Notes

Reaction equation

HRID 228522 reaction equation
[NH2:1][C:2]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][CH:6]=1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(N(CC)CC)C.CN(C)C=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:16][O:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[O:17][CH3:18])[N:8]=[CH:7][CH:6]=[C:5]2[O:4][C:3]1[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:2]=1[NH:1][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 66827Phenylboronic AcidHCID 230785874-(2-Amino-4-methylphenoxy)-6,7-dimethoxyquinoline

Product 1

HCID 23156624N-[2-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methylphenyl]-N-phenylamineYield 77.2%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 22056947triethylamine N,N-dimethylformamideSolvent

Procedure

4-(2-Amino-4-methylphenoxy)-6,7-dimethoxyquinoline (52 mg) was dissolved in triethylamine/N,N-dimethylformamide (0.5 ml/2.5 ml), and phenylboronic acid (100 mg) and copper acetate (250 mg) were added to the solution which was then stirred at room temperature overnight. The reaction solution was filtered, and the solvent was removed therefrom by distillation under the reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. Next, the ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using acetone-chloroform to give the title compound (50 mg, yield 76%).

Workup

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

Sources & evidence

ORD record
ord-cb2c590698844012b3e2a9628d8f6546
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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