Potassium Carbonate → 4-Pyridin-3-yl-benzoic acid

HRID 415279Notes

Reaction equation

HRID 415279 reaction equation
B([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)(O)O.Br[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:4]2[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=2)[CH:15]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 122863-BromopyridineHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 15152444-Pyridin-3-yl-benzoic acidYield 85.3%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-boronobenzoic acid (1.66 g, 10 mmol) and 3-bromopyridine (1.72 g, 11 mmol) in acetonitrile (40 mL) and water (40 mL), potassium carbonate (5.5 g, 40 mmol), bis(triphenylphosphine)palladium(II) chloride (400 mg, 0.37 mmol) were added. The mixture was degassed and purged withed nitrogen. The mixture was stirred under reflux for 24 h. Then the hot suspension was filtered and concentrated to half of the original volume and washed with dichloromethane. The aquatic phase was adjusted to pH=3 with hydrochloric acid (1 M) and filtrated, washed with water. The residue was dried in vacuum to obtain 1.7 g of white solid of 4-(pyridin-3-yl)benzoic acid. Yield: 85%. LC-MS (ESI) m/z: 200 (M+1)+.

Workup

  1. customThe mixture was degassed
  2. custompurged
  3. temperatureunder reflux for 24 h
  4. filtrationThen the hot suspension was filtered
  5. concentrationconcentrated to half of the original volume
  6. washwashed with dichloromethane
  7. filtrationfiltrated
  8. washwashed with water
  9. customThe residue was dried in vacuum

Sources & evidence

ORD record
ord-39502d25540f40518f6cd5409942661d
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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