1-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-cyano-5-(2-furyl)pyrazole → 1-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-cyano-1H-pyrazole 5-(2-furyl)pyrazole

HRID 394813노트

반응식

HRID 394813 반응식
FC(F)(F)C1C(C#N)=C(C(O)=O)NN=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[C:27]([C:28]3[O:29][CH:30]=[CH:31][CH:32]=3)=[C:26]([C:33]#[N:34])[C:25]([C:35]([F:38])([F:37])[F:36])=[N:24]2)=[CH:19][CH:18]=1.C(Cl)(Cl)(Cl)Cl.C(#N)C.O.I([O-])(=O)(=O)=O.[Na+]>O.[Ru](Cl)(Cl)Cl>[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH:27]=[C:26]([C:33]#[N:34])[C:25]([C:35]([F:38])([F:36])[F:37])=[N:24]2)=[CH:21][CH:22]=1.[O:29]1[CH:30]=[CH:31][CH:32]=[C:28]1[C:27]1[NH:23][N:24]=[CH:25][CH:26]=1

참가 물질

6

반응물 4

HCID 179399701-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-cyano-5-(2-furyl)pyrazoleHCID 22592919water acetonitrile CCl4HCID 23667635Sodium periodateHCID 178510177HCID 178510177, 화합물

생성물 1

HCID 696950671-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-cyano-1H-pyrazole 5-(2-furyl)pyrazole수율 102.6%

시약·촉매·용매 1

HCID 6093376Ruthenium trichloride hydrate촉매

실험 절차

1-(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-cyano-pyrazole-5-carboxylic acid. To a solution of 1-[(4-methoxy)phenyl]-3-(trifluoromethyl)-4-cyano-5-(2-furyl)pyrazole (0.68 g, 2.04 mmol) in 4:4:6 carbon tetrachloride/acetonitrile/water was added sodium periodate (1.96 g, 9.2 mmol) and ruthenium (III) chloride monohydrate (42 mg, 0.20 mmol). The resulting biphasic reaction was stirred vigorously at ambient temperature for 24 h. The reaction was quenched with 10% aq HCl and diluted with ethyl acetate. The organics were washed with brine, dried (MgSO4), filtered through a pad of Celite and concentrated. The residue was dissolved in 1:1 hexanes/ethyl acetate and extracted with sat'd aq Na2CO3 (2 times). The combined aqueous extracts were acidified and extracted with ethyl acetate. The ethyl acetate extracts were washed with brine, dried (MgSO4) and concentrated to afford 0.42 g (67%) of the title compound as a solid. LRMS (ES−): 310.0 (M−H)−.

후처리

  1. customThe resulting biphasic reaction
  2. customThe reaction was quenched with 10% aq HCl
  3. additiondiluted with ethyl acetate
  4. washThe organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered through a pad of Celite
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in 1:1 hexanes/ethyl acetate
  9. extractionextracted with sat'd aq Na2CO3 (2 times)
  10. extractionextracted with ethyl acetate
  11. washThe ethyl acetate extracts were washed with brine
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4b974a9b010d47c9abb4649bdc43c2ab
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06602895B2

반응 노트

불러오는 중…