Potassium Carbonate → 2-(2-fluorophenyl)quinoline

HRID 2308147Notes

Reaction equation

HRID 2308147 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>COCCOC.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]>[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 119282-ChloroquinolineHCID 27343542-Fluorophenylboronic acid

Product 1

HCID 116226842-(2-fluorophenyl)quinolineYield 96%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Chloroquinoline (4.9 g, 30 mmol), 2-fluorophenylboronic acid (5.0 g, 36 mmol) and K2CO3 (12 g) were dissolved in the solvent mixture of 50 mL ethylene glycol dimethyl ether and 75 mL water. To the stirred solution was added 1.7 g tetrakis(triphenylphosphine)palladium(O) and the mixture refluxed under N2 for 20 hours. The reaction mixture was cooled and the water extracted with methylene chloride three times. The combined organic phase was washed with portions of brine. The organic layer was then dried with anhydrous sodium sulfate, filtered, and evaporated of solvent. The crude material was purified on a silica gel column to give 2-(2-fluorophenyl)quinoline (6.4 g, 96% yield).

Workup

  1. temperaturethe mixture refluxed under N2 for 20 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionthe water extracted with methylene chloride three times
  4. washThe combined organic phase was washed with portions of brine
  5. dry with materialThe organic layer was then dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated of solvent
  8. customThe crude material was purified on a silica gel column

Sources & evidence

ORD record
ord-9209377f64764917849a24eee2c075f5
Source dataset
uspto-grants-2004_12
Patent number
US06835469B2

Reaction notes

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