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

HRID 545073노트

반응식

HRID 545073 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b877ee99b58b40699f4e90532de82053
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935702B2

반응 노트

불러오는 중…