497833-05-3

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromo-2-methyl-5-(trifluoromethyl)pyrazole-3-carboxylic acid is used as a reactant in the synthesis of 1-methyl-3-(trifluoromethyl)-N-[4-sulfonylphenyl]-1H-pyrazole-5-carboxamide, a nonpeptidic measles virus inhibitor. This application is significant because it contributes to the development of antiviral drugs that can help combat measles virus infections.
In the synthesis process, 4-Bromo-2-methyl-5-(trifluoromethyl)pyrazole-3-carboxylic acid serves as a key building block, providing the necessary structural features that enable the formation of the final product, a measles virus inhibitor. This inhibitor is designed to interfere with the replication and spread of the measles virus, thereby offering a potential treatment option for individuals affected by the virus.

Upstream product

• 154471-65-5 1-methyl-3-trifluoromethylpyrazol 
• 124-38-9 carbon dioxide 
• 497832-99-2 4-bromo-1-methyl-3-(trifluoromethyl)-1H-pyrazole 

Relevant academic research and scientific papers

Switchable reactivity: The site-selective functionalization of trifluoromethyl-substituted pyrazoles

Modern organometallic methods enable the regioflexible conversion of simple heterocyclic starting materials into families of isomers and congeners. Depending on the choice of the reagent, 1-methyl-5-(trifluoromethyl)pyrazole (1) undergoes deprotonation and subsequent carboxylation mainly or exclusively at either the 4-position of the heterocycle or at the nitrogen-attached methyl group. Similarly, 1-phenyl-5-(trifluoromethyl)pyrazole (5) and 3-methyl-l-phenyl-5-(trifluoromethyl)pyrazole (8) are selectively attacked by lithium diisopropylamide at the heterocyclic 4-position and by butyllithium concomitantly at the 4-position and the ortho position of the phenyl ring. In contrast, metalation of 1-methyl-3-(trifluoromethyl)pyrazole (2) occurs only at the 5-position, whatever the organometallic or metal amide base. Further sites become accessible to functionalization if bromine is introduced into the heterocyclic or aromatic ring. This has been demonstrated with 4-bromo-1-methyl-5-(trifluoromethyl)pyrazole (3), 4-bromo-l-methyl-3-(trifluoromethyl)pyrazole (4), 4-bromo-1-methyl-5-(trifluoromethyl)pyrazole (7) and 1-(2-bromophenyl)-5-(trifluoromethyl)pyrazole (6). Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.