Potassium Carbonate → HCID 58871256, compound

HRID 570083Notes

Reaction equation

HRID 570083 reaction equation
B([O-])([O-])O[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[CH:4]=1.Cl[C:13]1[CH:22]=[C:21]([CH3:23])[C:20]2[C:15](=[CH:16][CH:17]=[C:18](C)[CH:19]=2)[N:14]=1.[C:25](=O)([O-])[O-].[K+].[K+]>C1COCC1.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH3:9][C:5]1[CH:4]=[C:3]([C:13]2[CH:22]=[C:21]([CH3:23])[C:20]3[C:15](=[CH:16][C:17]([CH3:25])=[CH:18][CH:19]=3)[N:14]=2)[CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 6057692-Chloro-4,6-dimethylquinolineHCID 866123723-Methylphenyl borate

Product 1

HCID 58871256HCID 58871256, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

3-Methylphenyl borate (1.3 mmol), 2-chloro-4,6-dimethylquinoline (1 mmol), tetrakis(triphenylphosphine)palladium(O) (0.05 mmol) and potassium carbonate (3 mmol) were dissolved in THF (30 mL) and H2O (10 mL). The resulting solution was stirred in a bath at 100° C. for 24 hours. After completion of the reaction, the solvents were removed. The reaction mixture was extracted with dichloromethane and water and distilled under reduced pressure. The resulting residue was purified by silica gel column chromatography. The eluate was distilled under reduced pressure. The residue was recrystallized from dichloromethane and petroleum ether, and filtered to yield 2-(3-methylphenyl)-4,7-dimethylquinoline as a solid.

Workup

  1. customAfter completion of the reaction
  2. customthe solvents were removed
  3. extractionThe reaction mixture was extracted with dichloromethane and water
  4. distillationdistilled under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography
  6. distillationThe eluate was distilled under reduced pressure
  7. customThe residue was recrystallized from dichloromethane and petroleum ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-eae44b0bdc714add863ffbc050f2673a
Source dataset
uspto-grants-2015_05
Patent number
US09023489B2

Reaction notes

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