Potassium Carbonate → 4-Ethenyl-3,8-difluoro-6-methoxyquinoline

HRID 638995Notes

Reaction equation

HRID 638995 reaction equation
Br[C:2]1[C:11]2[C:6](=[C:7]([F:14])[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[F:15].C(=O)([O-])[O-].[K+].[K+].[CH:22](B)=[CH2:23]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:22]([C:2]1[C:11]2[C:6](=[C:7]([F:14])[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[F:15])=[CH2:23]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 685768324-Bromo-3,8-difluoro-6-methoxyquinolineHCID 178419161HCID 178419161, compound

Product 1

HCID 590260924-Ethenyl-3,8-difluoro-6-methoxyquinolineYield 90%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

4-Bromo-3,8-difluoro-6-(methoxy)quinoline (0.63 g, 2.3 mmol) in DME (26 mL) under argon, was treated with tetrakis(triphenylphosphine)palladium(0) (0.13 g, 0.115 mmol) and the mixture stirred at room temperature for 20 minutes. Anhydrous potassium carbonate (0.32 g, 2.3 mmol), water (7 mL), and vinylborane:pyridine complex (see F. Kerins and D O'Shea J. Org. Chem. 2002, 67, 4968-4971) (0.22 g, 0.92 mmol) were added and the mixture was heated at 100° C. for 2 hr. It was cooled, diluted with water and extracted with ether, dried over magnesium sulfate and evaporated to dryness. After work-up the product was chromatographed on silica gel, eluting with 10% methanol in DCM to afford a white solid (0.46 g, 90%). MS (+ve ion electrospray) m/z 221 (MH+).

Workup

  1. temperaturethe mixture was heated at 100° C. for 2 hr
  2. temperatureIt was cooled
  3. extractionextracted with ether
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customAfter work-up the product was chromatographed on silica gel
  7. washeluting with 10% methanol in DCM

Sources & evidence

ORD record
ord-6d85d8f564a74eefa82a3f5dc902e62a
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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