2-Chlorophenylboronic acid → HCID 57722982, compound

HRID 1987028Notes

Reaction equation

HRID 1987028 reaction equation
Br[C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:21])[N:7]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20].[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O>C1(C)C=CC=CC=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[N:7]1[C:8]2[C:3](=[C:2]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[Cl:22])[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=2)[CH2:4][CH2:5][C:6]1=[O:21]

Participants

7

Reactant 2

HCID 27343222-Chlorophenylboronic acidHCID 57722976HCID 57722976, compound

Product 1

HCID 57722982HCID 57722982, compoundYield 87%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 10340Sodium CarbonateSolvent

Procedure

5-Bromo-1-(2-chlorophenyl)-7-methoxy-3,4-dihydro-2(1H)-quinolinone (2.10 g, 5.728 mmol), and 2-chlorophenylboronic acid (1.77 g, 11.32 mmol) were dissolved in toluene (40 ml)-ethanol (15 ml), and 1M aqueous sodium carbonate (15 ml) added. Nitrogen gas was passed through the mixture for 2 min., then tetrakis(triphenylphosphine)-palladium(0) (0.3 g) added, and the mixture stirred under reflux under nitrogen for 3.5 h. The organic phase was separated, dried (Na2SO4), and evaporated in vacuo and the residue purified by flash chromatography over silica (70 g) eluting with cyclohexane-ethyl acetate gradient to afford the title compound as a white solid (1.98 g, 87%)

Workup

  1. additionadded
  2. temperatureunder reflux under nitrogen for 3.5 h
  3. customThe organic phase was separated
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customthe residue purified by flash chromatography over silica (70 g)
  7. washeluting with cyclohexane-ethyl acetate gradient

Sources & evidence

ORD record
ord-0b75f3e7170c441ea060a3ce00702e44
Source dataset
uspto-grants-2009_06
Patent number
US07550480B2

Reaction notes

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