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

HRID 1071487Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 100 °C

Procedure

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)+.

Workup

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

Sources & evidence

ORD record: ord-639adf11ed5b404195f2004a8aa9c246
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06906070B2

Reaction notes

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