Potassium Carbonate → Methyl 4-(4-pyridinyl)benzoate

HRID 478644Notes

Reaction equation

HRID 478644 reaction equation
COB([C:5]1[CH:10]=[CH:9][C:8]([C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)O.Br[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.[C:21](=O)([O-])[O-].[K+].[K+]>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:21][O:13][C:11](=[O:12])[C:8]1[CH:7]=[CH:6][C:5]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 142684-BromopyridineHCID 66904666HCID 66904666, compound

Product 1

HCID 5152686Methyl 4-(4-pyridinyl)benzoate

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-Carboxybenzeneboronic acid methyl ester (248 mmol) from A, 4-bromopyridine (248 mmol), tetrakis-(triphenylphosphin)-palladium (2.5 mmol) and potassium carbonate (744 mmol) are suspended in 1,2-dimethoxyethane (1100 ml). The stirred mixture is heated under reflux for 8 hours. After cooling the solvent is evaporated and water is added to the residue which is then extracted three times with ethyl acetate. The combined extract is dried over sodium sulfate and evaporated. The residue is suspended in diethylether and the solid filtered of and dried (vacuum). A pale-brown powder with mp. 99-101° C., Rf=0.39 (CH2Cl2/MeOH=95:5) is obtained.

Workup

  1. temperatureThe stirred mixture is heated
  2. temperatureunder reflux for 8 hours
  3. temperatureAfter cooling the solvent
  4. customis evaporated
  5. additionwater is added to the residue which
  6. extractionis then extracted three times with ethyl acetate
  7. extractionThe combined extract
  8. dry with materialis dried over sodium sulfate
  9. customevaporated
  10. filtrationthe solid filtered of and
  11. customdried (vacuum)
  12. customA pale-brown powder with mp. 99-101° C., Rf=0.39 (CH2Cl2/MeOH=95:5) is obtained

Sources & evidence

ORD record
ord-d1bf3cdcade547f1abde3374dfe4e52c
Source dataset
uspto-grants-2003_11
Patent number
US06642239B2

Reaction notes

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