Potassium Carbonate → 8-Methoxy-2-methyl-5-phenylquinoline

HRID 1108602Notes

Reaction equation

HRID 1108602 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:14])=[N:7]2.[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cl-].C(O)C.C1(C)C=CC=CC=1>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:2]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:3]2[C:8]=1[N:7]=[C:6]([CH3:14])[CH:5]=[CH:4]2

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 47150215-Bromo-8-methoxy-2-methylquinoline

Product 1

HCID 97949188-Methoxy-2-methyl-5-phenylquinolineYield 54%

Reagents, catalysts & solvents 4

HCID 178478903HCID 178478903, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

5-Bromo-8-methoxy-2-methylquinoline (509 mg) and benzene boronic acid (323 mg) were added to a mixture of 2 M aqueous potassium carbonate (2 ml), toluene (10 ml) and ethanol (1 ml) and refluxed for 30 minutes under a nitrogen atmosphere. The mixture was cooled, triphenylphosphine (75 mg) and dichlorobis(triphenylphosphine)palladium chloride (66 mg) were added and the mixture was heated at 60° C. overnight. After cooling, the reaction mixture was diluted with ethyl acetate (30 ml). The organic phase was washed with 2 M aqueous potassium carbonate solution (2×30 ml), dried (magnesium sulphate), filtered and evaporated in vacuo to give the title compound (272 mg) as an off-white solid.

Workup

  1. temperaturerefluxed for 30 minutes under a nitrogen atmosphere
  2. temperatureThe mixture was cooled
  3. temperatureAfter cooling
  4. washThe organic phase was washed with 2 M aqueous potassium carbonate solution (2×30 ml)
  5. dry with materialdried (magnesium sulphate)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-557e9858d6c14a05aa553bec09bf81d5
Source dataset
uspto-grants-2000_05
Patent number
US06069151

Reaction notes

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