1-Aryl 1,2,4-triazoles can be difficult to synthesize efficiently on large scale. Some of the challenges encountered when preparing this type of chemical architecture arise from the limitations associated with traditional triazole synthesis methodologies: Multiple steps to prepare and condense hydrazine derivatives, transition metal mediated C-N bond coupling (removal of catalyst by-products), and SNAr-type chemistry of a halogenated arene with a 1,2,4-triazole nucleophile, where a mixture of N-regio isomers are formed. To address these challenges, a new synthesis of 1-aryl 1,2,4-triazoles was created in the Chemical Development (CD) department at Bristol-Myers Squibb, and used to efficiently forge the 1,2,4-triazole subunits of several chemical intermediates. This new methodology dramatically reduced the waste footprint of the triazole forming reaction and underlines BMS's commitment to developing efficient and innovative green chemical processes.

Discovery, development, and application of a multi-component synthesis of 1-aryl 1,2,4-triazoles

248th National Meeting (2014)

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