jo9804339_si_001.pdf (869.14 kB)
Efficient Pyridinylmethyl Functionalization: Synthesis of 10,10-Bis[(2-fluoro-4-pyridinyl)methyl]-9(10H)-anthracenone (DMP 543), an Acetylcholine Release Enhancing Agent†
journal contribution
posted on 2000-10-21, 00:00 authored by Jaan A. Pesti, George F. Huhn, Jianguo Yin, Yide Xing, Joseph M. Fortunak, Richard A. Earl2-Fluoro-4-methylpyridine (3) is efficiently functionalized by chlorination, hydrolysis and methanesulfonylation into the novel alkylating agent 7. This mesylate is used for the bisalkylation of
anthrone under carefully defined conditions to prepare the cognition enhancer drug candidate 1.
This process proceeds in up to 37% overall yield and is adaptable for large scale synthesis.