Synthesis of Mavatrep: A Potent Antagonist of Transient Receptor Potential Vanilloid‑1

The process development of Mavatrep (1), a potent transient receptor potential vanilloid-1 (TRPV1) antagonist, is described. The two key synthetic transformations are the synthesis of (E)-6-bromo-2-(4-(trifluoromethyl)­styryl)­1H-benzo­[d]­imidazole (4) and the Suzuki coupling of 4 with 3,3-dimethyl-3H-benzo­[c]­[1,2]­oxaborol-1-ol (5). Compound 1a was prepared in four chemical steps in 63% overall yield.