Sodium Carbonate → 6-Phenylpyridine-2-carboxylic Acid

HRID 1171502Notes

Reaction equation

HRID 1171502 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>COCCOC>[C:17]1([C:2]2[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 5939196-Bromopyridine-2-carboxylic acid

Product 1

HCID 27628846-Phenylpyridine-2-carboxylic AcidYield 2.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

6-Bromopicolinic acid (1.0 g) was dissolved in 1,2-dimethoxyethane (15 mL) prior to the addition of palladium tetrakistriphenylphoshine (572 mg), 2M Na2CO3 (5 mL), and phenyl boronic acid (905 mg). The resulting solution was heated at reflux for 48 h. After cooling, 1N HCL was added to adjust the pH<4. A white precipitate was formed and was removed by filtration. A small portion of the filtrate was purified by reverse phase HPLC (gradient elution, water/acetonitrile/TFA) to afford 6-phenylpicolinic acid (25 mg). MS found: (M+H)+=200.1.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 48 h
  3. temperatureAfter cooling
  4. addition1N HCL was added
  5. customA white precipitate was formed
  6. customwas removed by filtration
  7. customA small portion of the filtrate was purified by reverse phase HPLC (gradient elution, water/acetonitrile/TFA)

Sources & evidence

ORD record
ord-9c35509194414bbd98d25786f5b74b4c
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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