Potassium Carbonate → HCID 21044146, compound

HRID 2308152Notes

Reaction equation

HRID 2308152 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]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COCCOC>[F:12][C:13]1[CH:18]=[C:17]([F:19])[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 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 119282-ChloroquinolineHCID 27343342,4-Difluorophenylboronic acid

Product 1

HCID 21044146HCID 21044146, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Chloroquinoline (1.20 g, 12.2 mmol), 2,4-difluorophenylboronic acid (2.32 g, 14.7 mmol), were added to 10 mL of ethylene glycol dimethyl ether (DME) and 12 mL of a 2 M solution of potassium carbonate. Triphenylphosphine (0.32 g, 1.2 mmol) and palladium acetate (0.069 g, 0.3 mmol) were added to the stirred reaction mixture and refluxed for 17 hours under a nitrogen atmosphere. The mixture was cooled to room temperature and the aqueous phase was separated from the organic phase. The aqueous phase was extracted with 2×30 mL of ethyl acetate. The combined organic extracts were washed first with distilled water followed by brine. The solvent was dried over magnesium sulfate and concentrated to give 2-(2,4-difluorophenyl)quinoline (2.9 g, 98.6%) as a white solid.

Workup

  1. temperaturerefluxed for 17 hours under a nitrogen atmosphere
  2. customthe aqueous phase was separated from the organic phase
  3. extractionThe aqueous phase was extracted with 2×30 mL of ethyl acetate
  4. washThe combined organic extracts were washed first with distilled water
  5. dry with materialThe solvent was dried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b93c2d48aadf4d96a64cc06c9165d183
Source dataset
uspto-grants-2004_12
Patent number
US06835469B2

Reaction notes

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