Potassium Carbonate → 5-Methyl-2-phenylpyridine

HRID 2096086Notes

Reaction equation

HRID 2096086 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(COC)OC>[CH3:8][C:5]1[CH:6]=[N:7][C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 5642162-Bromo-5-methylpyridine

Product 1

HCID 474675-Methyl-2-phenylpyridineYield 84.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a 2 L flask, 45.0 g (262 mmol) of 6-bromo-3-methylpyridine, 38.3 g (314 mmol) of phenylboronic acid, 1.47 g (6.54 mmol) of palladium acetate, 6.86 g (26.2 mmol) of triphenylphosphine and 353 mL of 2M K2CO3 were added to 405 mL of dimethoxyethane. The mixture was heated at reflux for 20 hours and cooled to room temperature. The aqueous phase was extracted twice with 200 mL of ethyl acetate. The combined organic extractions were then extracted with brine and dried over magnesium sulfate. The filtrate was evaporated in vacuo and the resultant oil purified by Kugelehor distillation (190° C. @ 500 microns) to give 37.2 g (84.1% yield) of 3-methyl-6-phenylpyridine as white solids.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 20 hours
  3. extractionThe aqueous phase was extracted twice with 200 mL of ethyl acetate
  4. extractionThe combined organic extractions
  5. extractionwere then extracted with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe filtrate was evaporated in vacuo
  8. distillationthe resultant oil purified by Kugelehor distillation (190° C. @ 500 microns)

Sources & evidence

ORD record
ord-9486f43a5de045c7b976c0f133c65a79
Source dataset
uspto-grants-2013_05
Patent number
US08449990B2

Reaction notes

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