Dichloromethane → HCID 23022708, compound

HRID 1727852Notes

Reaction equation

HRID 1727852 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.[C:23]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24].ClCCl>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(N(CC)CC)C>[C:23]([C:27]1[CH:32]=[CH:31][C:30]([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:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 27343204-tert-Butylphenylboronic acid2×HCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline2×

Product 1

HCID 23022708HCID 23022708, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (689 mg) (starting compound A) and 4-t-butylphenylboronic acid (450 mg) (starting compound B) were dissolved in a mixed solution composed of dichloromethane (50 ml) and triethylamine (0.7 ml) to prepare a solution. Copper(II) acetate (450 mg) was added to the solution, and the mixture was stirred at room temperature for 16 hr. The mixture was filtered, and the filtrate was then concentrated to give a crude which was then purified by chromatography on silica gel to give the title compound (500 mg, yield 50%).

Workup

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

Sources & evidence

ORD record
ord-765b42220d74432bbeeda66e48d330d3
Source dataset
uspto-grants-2009_02
Patent number
US07495104B2

Reaction notes

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