Ethyl Acetate → HCID 59221980, compound

HRID 1910345Notes

Reaction equation

HRID 1910345 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:15]1([CH3:24])[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(COC)OC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:24][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][N:9]=2)[CH:3]=1

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 57668727HCID 57668727, compound

Product 1

HCID 59221980HCID 59221980, compoundYield 108.8%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 2-(3-bromophenyl)-5-methylpyridine (26.4 g, 106 mmol), o-tolylboronic acid (17.4 g, 128 mmol), palladium (II) acetate (0.60 g, 2.7 mmol), and triphenylphosphine (2.8 g, 10.7 mmol) in 215 mL of dimethoxyethane was added a solution of potassium carbonate (39.7 g, 287 mmol) in 145 mL of water. The reaction mixture was heated at reflux under a nitrogen atmosphere for 16 h and cooled. Ethyl acetate was added, and the aqueous phase was discarded. Evaporation of the organic phase after drying over magnesium sulfate yielded a yellow liquid that was then subjected to vacuum distillation at 160° C. to remove most of the impurities. Further distillation at 220° C. yielded 29.9 g of a colorless liquid that was further purified by silica gel column chromatography with 10/90 ethyl acetate/hexane as the eluent to give 22.5 g (81%) of pure 2-(2′-methylbiphenyl-3-yl)pyridine as a colorless, viscous liquid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under a nitrogen atmosphere for 16 h
  3. temperaturecooled
  4. customEvaporation of the organic phase
  5. dry with materialafter drying over magnesium sulfate
  6. customyielded a yellow liquid that
  7. distillationwas then subjected to vacuum distillation at 160° C.
  8. customto remove most of the impurities
  9. distillationFurther distillation at 220° C.

Sources & evidence

ORD record
ord-3988ef2d71a44e029de3eaa9a620e208
Source dataset
uspto-grants-2013_12
Patent number
US08603645B2

Reaction notes

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