Triethylamine → HCID 23022753, compound

HRID 1727853Notes

Reaction equation

HRID 1727853 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:21]=[CH:20]C(CN)=C[CH:17]=1.[CH2:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])C.[C:31]([C:35]1[CH:40]=CC(OB=O)=[CH:37][CH:36]=1)([CH3:34])([CH3:33])[CH3:32]>C(Cl)(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:31]([C:35]1[CH:36]=[CH:37][C:27]([N:26]([C:29]2[CH:30]=[CH:17][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:21][CH:20]=2)[CH3:24])=[CH:28][CH:40]=1)([CH3:34])([CH3:33])[CH3:32]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 69054245HCID 69054245, compoundHCID 69057670HCID 69057670, compound

Product 1

HCID 23022753HCID 23022753, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6212ChloroformSolvent

Procedure

[4-(6,7-Dimethoxy-4-quinolyloxy)phenyl]methylamine (100 mg) was dissolved in chloroform (10 ml) to prepare a solution. Triethylamine (0.3 ml), 4-tert-butylphenylboranic acid (100 mg), and copper(II) acetate (50 mg) were then added to the solution, and the mixture was stirred at room temperature for 3 days. The insolubles were removed by filtration, and the solvent was then removed by evaporation under the reduced pressure. The residue was purified by thin-layer chromatography on silica gel using chloroform/acetone for development to give the title compound (21 mg, yield 15%).

Workup

  1. customto prepare a solution
  2. customThe insolubles were removed by filtration
  3. customthe solvent was then removed by evaporation under the reduced pressure
  4. customThe residue was purified by thin-layer chromatography on silica gel

Sources & evidence

ORD record
ord-9d1829dd4aa94b9296b67bbce7943753
Source dataset
uspto-grants-2009_02
Patent number
US07495104B2

Reaction notes

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