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

HRID 2185015Notes

Reaction equation

HRID 2185015 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)([OH:3])=[O:2].Br[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:7]2[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=2)[CH:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 122863-BromopyridineHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 15152444-Pyridin-3-yl-benzoic acid

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 4-carboxybenzeneboronic acid (0.5 g, 2.9 mmol), 3-bromopyridine (0.46 g, 2.9 mmol), sodium carbonate (1.37 g), and tetrakis(triphenylphosphine)palladium(0) (0.1 g) in 50% aqueous 1,2-dimethoxyethane (70 mL) was heated to reflux for 16 h, cooled, acidified, and extracted with dichloromethane. The organic phase was dried and concentrated in vacuo to yield the title compound, which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 h
  3. temperaturecooled
  4. extractionextracted with dichloromethane
  5. customThe organic phase was dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-939fca7a571f4031adc4388a58222ded
Source dataset
uspto-grants-2002_06
Patent number
US06399656B1

Reaction notes

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