Triethylamine → 2-Ethenyl-6-fluoropyridine

HRID 230785Notes

Reaction equation

HRID 230785 reaction equation
[CH:1]([B-](F)(F)F)=[CH2:2].[K+].C(N(CC)CC)C.Br[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[N:17]=1.C(=O)([O-])O.[Na+]>C(O)CC>[F:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([CH:1]=[CH2:2])[N:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 6394382-Bromo-6-fluoropyridineHCID 23679353Potassium vinyltrifluoroborate

Product 1

HCID 690038492-Ethenyl-6-fluoropyridineYield 35.7%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
100 °C

Procedure

Potassium vinyltrifluoroborate (2.28 g), triethylamine (2.38 mL) and [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane complex (928 mg) were added in that order to an n-propanol solution (12 mL) of 2-bromo-6-fluoropyridine (2.0 g), and stirred at 100° C. for 11 hours, and then at room temperature for 2 days. Saturated sodium hydrogencarbonate solution was added to the reaction liquid, and extracted with ethyl acetate. The organic layer was washed with saturated saline water, dried, concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1) to obtain the entitled compound (500 mg).

Workup

  1. waitat room temperature for 2 days
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-2fdfa160f0a44b6a99e97b05f53a70f0
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Reaction notes

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