Ethyl 4-(furan-2-yl)-2,4-dioxobutanoate → Ethyl 1-(3-cyano-4-fluorophenyl)-5-(2-furyl)pyrazole-3-carboxylate

HRID 1071487노트

반응식

HRID 1071487 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=O)[CH2:7][C:8](=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10].[Sn](Cl)(Cl)(Cl)Cl.[F:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][NH2:29])=[CH:24][C:23]=1[C:30]#[N:31]>C(O)(=O)C>[C:30]([C:23]1[CH:24]=[C:25]([N:28]2[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)=[CH:7][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:29]2)[CH:26]=[CH:27][C:22]=1[F:21])#[N:31]

참가 물질

4

반응물 2

HCID 3006753Ethyl 4-(furan-2-yl)-2,4-dioxobutanoateHCID 688056624-Fluoro-3-cyanophenylhydrazine tin chloride

생성물 1

HCID 22288722Ethyl 1-(3-cyano-4-fluorophenyl)-5-(2-furyl)pyrazole-3-carboxylate수율 46%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

To ethyl 4-(2-furyl)-2,4-dioxobutyrate (3.5 g, 16.7 mmol) in 50 mL of glacial acetic acid was added 4-fluoro-3-cyanophenylhydrazine tin chloride (6.3 g, 16.7 mmol). The reaction was stirred at 100° C. for 4 h. The reaction was allowed to cool to room temperature and the acetic acid was removed in vacuo. The residue was diluted with ethyl acetate and the organics were washed with saturated aq NaHCO3 and brine, dried (MgSO4) and concentrated. The residue was purified by recrystallization from hexane/ethyl acetate to afford 2.5 g (46%) of the title compound. LRMS (ES+): 326.1 (M+H)+.

후처리

  1. temperatureto cool to room temperature
  2. customthe acetic acid was removed in vacuo
  3. additionThe residue was diluted with ethyl acetate
  4. washthe organics were washed with saturated aq NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by recrystallization from hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-639adf11ed5b404195f2004a8aa9c246
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06906070B2

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