Water → 2-Phenylpyridine

HRID 1282480Notes

Reaction equation

HRID 1282480 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8]1(OB(O)O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C(C2C=CC=CC=2)=C(P(C2CCCCC2)C2CCCCC2)C)C=CC=CC=1.C1(C)C=CC=CC=1>[C:8]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 962WaterHCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 78412Phenyl dihydrogen orthoborate

Product 1

HCID 138872-PhenylpyridineYield 85.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 12010824Cy-vBRIDPCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Into a reactor were introduced 0.79 g (5.0 mmol) of 2-bromo-pyridine, 0.73 g (6.0 mmol) of phenylboric acid, 1.38 g (10.0 mmol) of potassium carbonate, 11.2 mg (0.05 mmol) of palladium acetate, 39.1 mg (0.1 mmol) of the 1,1-diphenyl-2-(dicyclohexylphosphine)propene obtained in Example 2, 5.0 ml of water, and 15.0 ml of toluene under a nitrogen atmosphere. The resultant reaction mixture was stirred at 80° C. for 4 hours and then cooled. Thereafter, the solvent was removed under pressure. The concentrate was purified by column clromatography to obtain 0.66 g (85%) of 2-phenylpyridine as the target compound.

Workup

  1. customThe resultant reaction mixture
  2. temperaturecooled
  3. customThereafter, the solvent was removed under pressure
  4. customThe concentrate was purified by column clromatography

Sources & evidence

ORD record
ord-56c4cab6ce9e45f28b502ce006f5b393
Source dataset
uspto-grants-2002_09
Patent number
US06455720B1

Reaction notes

Loading…