104295-62-7

Usage

InChI:InChI=1/C11H12N2O3/c1-3-15-11(14)9-7-8(12-13(9)2)10-5-4-6-16-10/h4-7H,3H2,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 34020-22-9 ethyl 5-(furan-2-yl)-1H-pyrazole-3-carboxylate 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 36983-35-4 ethyl 4-(furan-2-yl)-2,4-dioxobutyrate 
• 60-34-4 methylhydrazine 
• 412304-91-7 ethyl 4-(2-furyl)-2,4-dioxobutanoate 

Downstream Products

• 100537-55-1 5-[2]furyl-1-phenyl-1H-pyrazole-3-carboxylic acid 
• 106166-52-3 5-[2]furyl-1-phenyl-1H-pyrazole 

Relevant academic research and scientific papers

Synthesis of fluorinated and nonfluorinated tebufenpyrad analogues for the study of anti-angiogenesis MOA

In this contribution we report the synthesis of fluorinated and nonfluorinated tebufenpyrad analogues to explore potential druglike properties through the phenotypic screening as part of the Lilly Open Innovation Drug Discovery (OIDD) program.

Improved regioselectivity in pyrazole formation through the use of fluorinated alcohols as solvents: Synthesis and biological activity of fluorinated tebufenpyrad analogs

(Chemical Equation Presented) The preparation of N-methylpyrazoles is usually accomplished through reaction of a suitable 1,3-diketone with methylhydrazine in ethanol as the solvent. This strategy, however, leads to the formation of regioisomeric mixtures of N-methylpyrazoles, which sometimes are difficult to separate. We have determined that the use of fluorinated alcohols such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvents dramatically increases the regioselectivity in the pyrazole formation, and we have used this modification in a straightforward synthesis of fluorinated analogs of Tebufenpyrad with acaricide activity.

Synthesis of new fluorinated tebufenpyrad analogs with acaricidal activity through regioselective pyrazole formation

(Chemical Equation Presented) In previous studies, our group has shown that the use of fluorinated alcohols such as trifluoroethanol (TFE) and hexafluoroisopropanol (HFIP) as solvents dramatically increases the regioselectivity in the pyrazole formation from 1,3-diketone with methylhydrazine. We have now applied this synthetic method to the preparation of new fluorinated pyrazoles, which have then been used as synthetic intermediates in the preparation of fluorinated analogs of Tebufenpyrad, a commercial acaricide. These compounds display a strong acaricidal activity that is either comparable to or better than that of the commercial compound.