Water → 4-(3-Methoxypyridin-2-yl)benzoic acid

HRID 1391428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1391428
Cl[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:10](=[O:13])([O-])[O-:11].[K+].[K+].O.[C:17](#N)[CH3:18]>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>[CH3:9][O:8][C:7]1[C:2]([C:18]2[CH:17]=[CH:7][C:6]([C:10]([OH:11])=[O:13])=[CH:5][CH:4]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 1042522-Chloro-3-methoxypyridine

Produkt 1

HCID 534262554-(3-Methoxypyridin-2-yl)benzoic acidAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

4-bis(hydroxyl)boron-1-methylbenzoate (2.8 mmol; 582 mg) was dissolved in acetonitrile (2 ml) and added to a 5 ml microwave vessel. To the solution was 3.5 mmol of 2-chloro-3-methoxypyridine (482 mg), 34 mg of tetrakis(triphenylphosphine)palladium(0). After stirring until dissolution, 8.4 mmol of potassium carbonate (1.16 g) was added, followed by 1 ml of water. The mixture was then heated at 160° C. for 300 seconds. After reaction completion, the solvents were evaporated under vacuum. The residue was dissolved in 2N KOH and THF and heated for 10 min. After hydrolysis, the THF was evaporated and the basic layer was washed with EtOAC. The aqueous layer was then acidified and extracted 3 times with EtOAc. The organic layers were combined and washed with water and brine. After drying, filtration and evaporation, the residue was triterated with ether to give the desired product as a yellow solid (423 mg; 77%).

Aufarbeitung

  1. additionadded to a 5 ml microwave vessel
  2. additionwas added
  3. customAfter reaction completion
  4. customthe solvents were evaporated under vacuum
  5. dissolutionThe residue was dissolved in 2N KOH
  6. temperatureTHF and heated for 10 min
  7. customAfter hydrolysis
  8. customthe THF was evaporated
  9. washthe basic layer was washed with EtOAC
  10. extractionextracted 3 times with EtOAc
  11. washwashed with water and brine
  12. customAfter drying
  13. filtrationfiltration and evaporation

Quellen und Nachweise

ORD-Eintrag
ord-21eee09d2ac64122b82f3ed3fe65fb49
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07338950B2

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