Potassium Carbonate → HCID 58871218, compound

HRID 570084Notes

Reaction equation

HRID 570084 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[C:22]([CH3:23])=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH3:24])[CH:19]=2)[N:14]=1.C(=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[C:22]([CH3:23])=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:24])[CH:19]=3)[N:14]=2)[CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 157075422-Chloro-3,6-dimethylquinolineHCID 866123723-Methylphenyl borate

Product 1

HCID 58871218HCID 58871218, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

3-Methylphenyl borate (1.3 mmol), 2-chloro-3,6-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 THF and the toluene were removed. The reaction solution 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)-3,6-dimethylquinoline as a solid.

Workup

  1. customAfter completion of the reaction
  2. customthe THF and the toluene were removed
  3. extractionThe reaction solution 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-000a72fb152148a0ba487b523f8e51a4
Source dataset
uspto-grants-2015_05
Patent number
US09023489B2

Reaction notes

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