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Early process development toward a triple reuptake inhibitor is described. Three different routes were evaluated; one of them was optimized and scaled up to generate 470 g of API as this route minimized the formation of undesired side products. The selected route featured Eatons reagent-mediated cyclization of a phenyl acetamide, copper-mediated Buchwald-Hartwig coupling to install a morpholine moiety, and palladium-catalyzed alpha-arylation of a dihydroisoquinolinone to construct the core structure.
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Reference：
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem