Potassium Phosphate, Tribasic → Methyl 3-(3-pyridinyl)benzoate

HRID 429383

Reaction equation

HRID 429383 reaction equation
C(B(CC)[C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)C.[CH3:12][O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17](I)[CH:16]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.O.[Pd]>[CH3:12][O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:4]2[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:16]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 69258Methyl 3-iodobenzoateHCID 6428513-(Diethylboryl)pyridine

Product 1

HCID 4133188Methyl 3-(3-pyridinyl)benzoateYield 68.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of diethyl(3-pyridyl)borane (176.4 g, 1.2mole), methyl-3-iodobenzoate(262 g, 1 mole), potassium phosphate (318.4 g, 1.5 mole) and tetrakistriphenlyphosphine palladium (0) (57.8 g, 0.05 mole) in DMF (1000 ml) was heated at 80 degrees under argon. After 10 h, the mixture was diluted with water and extracted with ethyl acetate. The organic layer was filtered and washed with water. To the organic fraction was added concentrated HCL (65 ml). The organic layer was separated and extracted with aqueous HCl. The combined acid extractions were treated with ethyl acetate, followed by 50% aqueous sodium hydroxide (55 ml). The organic layer was separated, washed with water and saturated sodium bicarbonate solution, then dried over sodium sulfate. The solution was filtered and concentrated to give methyl-3-(pyridin-3-yl)benzoate (145.3 g).

Workup

  1. temperaturewas heated at 80 degrees under argon
  2. extractionextracted with ethyl acetate
  3. filtrationThe organic layer was filtered
  4. washwashed with water
  5. additionTo the organic fraction was added
  6. concentrationconcentrated HCL (65 ml)
  7. customThe organic layer was separated
  8. extractionextracted with aqueous HCl
  9. extractionThe combined acid extractions
  10. additionwere treated with ethyl acetate
  11. customThe organic layer was separated
  12. washwashed with water and saturated sodium bicarbonate solution
  13. dry with materialdried over sodium sulfate
  14. filtrationThe solution was filtered
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-86b1a893ad314559a104aad99cb2cd51
Source dataset
uspto-grants-2001_11
Patent number
US06316466B1

Linked notes

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