BAY-1161116

A scalable and efficient synthesis of N-{trans-4-[(8-cyanoquinolin-4-yl)oxy]cyclohexyl}-3-fluorobenzamide (BAY 1161116), an androgen receptor antagonist was reported.The original synthesis included a low-yielding Mitsunobu reaction and employed cis-aminocyclohexanol, which was accessible only via a troublesome synthesis, as a key building block.The novel synthetic pathway starts from readily available trans-aminocyclohexanol and features a palladium-catalyzed etherification reaction in place of the Mitsunobu reaction as the key step.This four-step synthesis could be performed reliably on a multikilogram scale and purification of all intermediates as well as the final product could be achieved by simple extraction and crystallization procedures.