The Syntheses of 3-Substituted 4-(Pyridin-2-ylthio)indoles via Leimgruber-Batcho Indole Synthesis

摘要

We have designed a new family of radioligands,3-(amino- and hydroxymethyl)-4-(5-iodopyridin-2-ylthio)indoles,combining characteristically distinct moieties proven to impart successful binding ability in a variety of structurally diverse selective serotonin reuptake inhibitors recently published.Described in this article are the syntheses of 3-substituted 4-(5-iodopyridin-2-ylthio)-indoles,featuring successful adaptation of the modified Leimgruber-Batcho indole synthesis onto the key intermediate l-(5-iodopyridin-2-ylthio)-2-methyl-3-nitrobenzene (6) prepared from the nucleophilic aromatic substitution of chloropyridine 7 with thiophenol 8.