Sodium Carbonate → 6-Phenylpyridine-2-carboxylic Acid

HRID 1367911Notes

Reaction equation

HRID 1367911 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[C:11]1([C:2]2[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

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

Product 1

HCID 27628846-Phenylpyridine-2-carboxylic AcidYield 51.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution 1.0 g (4.9 mmol) of 6-bromo-pyridine-2-carboxylic acid, 0.9 g (7.4 mmol) of phenylboronic acid, 0.4 g (0.36 mmol) of palladium tetrakistriphenyl phosphine in 25 mL of DME was added 9.9 mL of 2 N Na2CO3 solutions under nitrogen. After 12 h reflux under nitrogen, the reaction mixture was cooled and filtered through a filter paper. The filtrate was acidified using 2 N HCl (pH=5). The resulting white precipitate was filtered, washed with water and dried to afford 0.5 g (51%) of 6-phenyl-pyridine-2-carboxylic acid. LCMS: 200 (M+1)+

Workup

  1. temperatureAfter 12 h reflux under nitrogen
  2. temperaturethe reaction mixture was cooled
  3. filtrationfiltered through a filter paper
  4. filtrationThe resulting white precipitate was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-da78616a60d24f2bbf0e18f6413aa5f3
Source dataset
uspto-grants-2011_02
Patent number
US07893267B2

Reaction notes

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