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A Convergent Approach To The Continuous Synthesis Of Telmisartan Via A Suzuki Reaction Between Two Functionalized Benzimidazoles, Alex D. Martin
A Convergent Approach To The Continuous Synthesis Of Telmisartan Via A Suzuki Reaction Between Two Functionalized Benzimidazoles, Alex D. Martin
Theses and Dissertations
A direct and highly efficient synthesis has been developed for telmisartan, the active ingredient in the widely prescribed antihypertensive drug Micardis®. This approach brings together two functionalized benzimidazoles using a high-yielding Suzuki reaction that can be catalyzed by a homogeneous palladium source or palladium on a solid support.
The ability to perform the cross-coupling reaction was facilitated by the regio-controlled preparation of a 2-bromo-1-methylbenzimidazole precursor. The method developed is the first reported selective bromination at the 2-position of a benzimidazole and produces the first major precursor in high yield (93%). The second precursor, potassium (4-methyl-2-propylbenzimidazol-6-yl) trifluoroborate, was prepared from commercially …