Triethylamine → HCID 44382259, compound

HRID 1727856Notes

Reaction equation

HRID 1727856 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:19]([OH:22])=[CH:18][CH:17]=1.C(N(CC)CC)C.[C:30]([C:34]1[CH:39]=[CH:38][C:37](OB=O)=[CH:36][CH:35]=1)([CH3:33])([CH3:32])[CH3:31]>C(Cl)(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:30]([C:34]1[CH:39]=[CH:38][C:37]([O:22][C:19]2[CH:18]=[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)=[CH:36][CH:35]=1)([CH3:33])([CH3:32])[CH3:31]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 17755508HCID 17755508, compound2×HCID 69054245HCID 69054245, compound

Product 1

HCID 44382259HCID 44382259, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6212ChloroformSolvent

Procedure

4-(6,7-Dimethoxy-4-quinolyloxy)phenol (starting compound 8) (24 mg) was dissolved in chloroform (2 ml) to prepare a solution. Triethylamine (0.3 ml), 4-tert-butylphenylboranic acid (50 mg), and copper(II) acetate (90 mg) were added to the solution, and the mixture was stirred at room temperature for 4 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 (20 mg, yield 58%).

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-ddaa94e8a06a4bf29dc50ecf8bea5ed2
Source dataset
uspto-grants-2009_02
Patent number
US07495104B2

Reaction notes

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