Sodium Carbonate → 6-Phenylpyridine-2-carboxylic Acid

HRID 2225200Notes

Reaction equation

HRID 2225200 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

Preparation H9, Step 1: 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. customPreparation H9, Step 1
  2. temperatureThe resulting solution was heated
  3. temperatureat reflux for 48 h
  4. temperatureAfter cooling
  5. addition1N HCL was added
  6. customA white precipitate was formed
  7. customwas removed by filtration
  8. customA small portion of the filtrate was purified by reverse phase HPLC (gradient elution, water/acetonitrile/TFA)

Sources & evidence

ORD record
ord-ab3cf80528b649259fbc8ccb8d48393c
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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