Dichloromethane → (4-Bromophenyl)-[4-(6,7-dimethoxy-4-quinolyloxy)phenyl]amine

HRID 1727863Notes

Reaction equation

HRID 1727863 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[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.[Br:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.ClCCl>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(N(CC)CC)C>[Br:23][C:24]1[CH:29]=[CH:28][C:27]([NH:20][C:19]2[CH:21]=[CH:22][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:17][CH:18]=2)=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 79599(4-Bromophenyl)boronic acidHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 23022618(4-Bromophenyl)-[4-(6,7-dimethoxy-4-quinolyloxy)phenyl]amineYield 46%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (100 mg) and 4-bromophenylboronic acid (80 mg) were dissolved in a mixed solution composed of dichloromethane (5 ml) and triethylamine (0.07 ml) to prepare a solution. Copper(II) acetate (50 mg) was added to the solution, and the mixture was stirred at room temperature for 16 hr. The stirred mixture was filtered, and the filtrate was then concentrated. The crude thus obtained was purified by chromatography on silica gel to give (4-bromophenyl)-[4-(6,7-dimethoxy-4-quinolyloxy)phenyl]amine (70 mg).

Workup

  1. customto prepare a solution
  2. filtrationThe stirred mixture was filtered
  3. concentrationthe filtrate was then concentrated
  4. customThe crude thus obtained
  5. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-da001c612dea48c0853ac7ddc33a687f
Source dataset
uspto-grants-2009_02
Patent number
US07495104B2

Reaction notes

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