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Development of a Two-Step Route to 3-PBC and βCCt, Two Agents Active against Alcohol Self-Administration in Rodent and Primate Models

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journal contribution
posted on 03.06.2011, 00:00 by Ojas A. Namjoshi, Angelica Gryboski, German O. Fonseca, Michael L. Van Linn, Zhi-jian Wang, Jeffrey R. Deschamps, James M. Cook
To gain access to 3-propoxy-β-carboline hydrochloride (3-PBC·HCl) (1·HCl) and β-carboline-3-carboxylate-tert-butyl ester (βCCt) (2), potential clinical agents active against alcohol self-administration, a two-step route was developed. This process involves a palladium-catalyzed Buchwald–Hartwig coupling and an intramolecular Heck reaction. This two-step route provides rapid access to multigram quantities of 3-PBC (1) and βCCt (2), as well as analogues for studies of alcohol self-administration. The overall yield of 3-PBC (1) was improved from 8% to 50% by this route.