Butyl vinyl ether → 2-Acetyl-5-amino-3-trifluoromethylpyridine

HRID 545073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 545073
Cl[C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH:42]([O:44]CCCC)=[CH2:43].C([O-])(O)=O.[Na+]>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:8][C:5]1[CH:4]=[C:3]([C:9]([F:12])([F:11])[F:10])[C:2]([C:42](=[O:44])[CH3:43])=[N:7][CH:6]=1

Komponenten

7

Edukt 4

HCID 8108Butyl vinyl etherHCID 812191,3-Bis(diphenylphosphino)propaneHCID 516892Sodium BicarbonateHCID 135322446-Chloro-5-(trifluoromethyl)pyridin-3-amine

Produkt 1

HCID 586455412-Acetyl-5-amino-3-trifluoromethylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Heat a mixture of 6-chloro-5-trifluoromethyl-pyridin-3-ylamine (985 mg, 5.0 mmol), palladium acetate (20 mg), DPPP (60 mg), butyl vinyl ether (1.5 g, 15 mmol) and NaHCO3 (840 mg, 10 mmol) in MeOH (10 mL) at 130° C. for 18 hours. Cool, filter and wash the solid with MeOH. Add 6M hydrochloric acid (5 mL), stir for 1 hour and evaporate the volatiles. Dissolve the residue in EtOAc (50 mL) and wash with saturated NaHCO3(aq) (50 mL) and brine (50 mL). Dry the organic extract over MgSO4 and remove the solvent under reduced pressure to yield the title compound.

Aufarbeitung

  1. temperatureHeat
  2. temperatureCool
  3. filtrationfilter
  4. washwash the solid with MeOH
  5. additionAdd 6M hydrochloric acid (5 mL)
  6. customevaporate the volatiles
  7. dissolutionDissolve the residue in EtOAc (50 mL)
  8. washwash with saturated NaHCO3(aq) (50 mL) and brine (50 mL)
  9. customDry the
  10. extractionorganic extract over MgSO4
  11. customremove the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b877ee99b58b40699f4e90532de82053
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935702B2

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