An alternative synthesis of the antidepressant Navacaprant

An eight-step synthetic route has been developed for the antidepressant Navacaprant starting from 4-bromo-2-fluoroaniline in 4.7% overall yield, the key step having been the replacement of the 4-positioned bromine atom by the ethyl group employing the Suzuki–Miyaura method. This new protocol offers three key advantages, namely, the use of an inexpensive starting material, independent construction of the quinoline and 1,2,4-oxadiazole moieties, and the introduction of the 4-(tetrahydropyran-4-ylamino)piperidino substituent in a single step.