Potassium Carbonate → 5-Bromo-2-phenylpyridine

HRID 1897971Notes

Reaction equation

HRID 1897971 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.O>[C:9]1([C:2]2[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 693532,5-Dibromopyridine

Product 1

HCID 27628625-Bromo-2-phenylpyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture is prepared of 2,5-dibromopyridine (10 g, 42.21 mmol), phenylboronic acid (5.1 g, 42.21 mmol), and potassium carbonate (11.7 g, 84.42 mmol) in 100 mL dimethoxyethane and 40 mL of water. Nitrogen is bubbled directly into the mixture for 30 minutes. Next, tetrakis(triphenylphosphine)palladium(0) was added (244 mg, 2.11 mmol) and the mixture is heated to reflux under nitrogen overnight. The mixture is cooled and diluted with ethyl acetate and water. The layers are separated and the aqueous layer is extracted with ethyl acetate. The organic layers are washed with brine, dried over magnesium sulfate, filtered, and evaporated to a residue. The residue is purified by column chromatography eluting with 0, 2, and 5% ethyl acetate/hexanes.

Workup

  1. customNitrogen is bubbled directly into the mixture for 30 minutes
  2. additionNext, tetrakis(triphenylphosphine)palladium(0) was added (244 mg, 2.11 mmol)
  3. temperaturethe mixture is heated
  4. temperatureto reflux under nitrogen overnight
  5. temperatureThe mixture is cooled
  6. additiondiluted with ethyl acetate and water
  7. customThe layers are separated
  8. extractionthe aqueous layer is extracted with ethyl acetate
  9. washThe organic layers are washed with brine
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. customevaporated to a residue
  13. customThe residue is purified by column chromatography
  14. washeluting with 0, 2, and 5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-ff0cd77e6e794dc28aa90df86b887912
Source dataset
uspto-grants-2013_08
Patent number
US08519384B2

Reaction notes

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