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

HRID 545073ノート

反応式

HRID 545073 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b877ee99b58b40699f4e90532de82053
出典データセット
uspto-grants-2011_05
特許番号
US07935702B2

反応ノート

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