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 394813ノート

反応式

HRID 394813 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6093376Ruthenium trichloride hydrate触媒

実験手順

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)−.

後処理

  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

出典と根拠

ORDレコード
ord-4b974a9b010d47c9abb4649bdc43c2ab
出典データセット
uspto-grants-2003_08
特許番号
US06602895B2

反応ノート

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