Sodium Carbonate → Ethyl 3-(pyridin-4-yl)benzoate

HRID 628840Notes

Reaction equation

HRID 628840 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[C:8]([C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1)([O:10][CH2:11][CH3:12])=[O:9].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O.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:5]1[CH:6]=[CH:7][C:2]([C:17]2[CH:18]=[C:13]([CH:14]=[CH:15][CH:16]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 142684-BromopyridineHCID 3249312(3-Ethoxycarbonylphenyl)boronic acid

Product 1

HCID 11356603Ethyl 3-(pyridin-4-yl)benzoateYield 86%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Part A. A solution of 4-bromopyridine (1.0 g, 5.2 mmol) in acetonitrile-water (10 mL/5 mL) is treated with 3-carboethoxybenzeneboronic acid (0.93 g, 5.2 mmol), sodium carbonate (2.2 g, 21 mmol) and catalytic tetrakis(triphenylphosphine)palladium. The solution is heated to reflux for 12 h., then cooled and extracted with ethyl acetate. The extract is washed with brine, dried over sodium sulfate, filtered and evaporated. The residual material is separated by flash chromatography to afford ethyl 3-pyridin-4-yl-benzoate (1.0 g, 86%).

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux for 12 h.
  3. temperaturecooled
  4. extractionextracted with ethyl acetate
  5. washThe extract is washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residual material is separated by flash chromatography

Sources & evidence

ORD record
ord-76075450783f4d5dbecf631951e4a502
Source dataset
uspto-grants-2016_04
Patent number
US09315467B2

Reaction notes

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