Ethyl 5,5,5-trifluoro-2,4-dioxopentanoate → ethyl 1-cyclopropyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylate

HRID 873875Notes

Reaction equation

HRID 873875 reaction equation
[CH:1]1([NH:4][NH2:5])[CH2:3][CH2:2]1.[F:6][C:7]([F:19])([F:18])[C:8](=O)[CH2:9][C:10](=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12]>>[CH:1]1([N:4]2[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][C:8]([C:7]([F:6])([F:18])[F:19])=[N:5]2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 19576760Ethyl 5,5,5-trifluoro-2,4-dioxopentanoateHCID 19594968Cyclopropylhydrazine

Product 1

HCID 117702900ethyl 1-cyclopropyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylate

Procedure

The title compound was prepared in analogy to the procedure described in Step 17.3 using cyclopropylhydrazine (Step 17.2) and ethyl 5,5,5-trifluoro-2,4-dioxopentanoate at 100° C. for 2 hr. The crude product was purified by silica gel column chromatography (hexane/EtOAc 9:1). tR: 1.23 min (LC-MS 2); ESI-MS: 249.2 [M+H]+ (LC-MS 2); Rf=0.34 (hexane/EtOAc 9:1).

Workup

  1. customThe crude product was purified by silica gel column chromatography (hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-30444e273544436aa3b174fd8d2ebb40
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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