10.1021/jo9804339.s001 Jaan A. Pesti Jaan A. Pesti George F. Huhn George F. Huhn Jianguo Yin Jianguo Yin Yide Xing Yide Xing Joseph M. Fortunak Joseph M. Fortunak Richard A. Earl Richard A. Earl Efficient Pyridinylmethyl Functionalization:  Synthesis of 10,10-Bis[(2-fluoro-4-pyridinyl)methyl]-9(10<i>H</i>)-anthracenone (DMP 543), an Acetylcholine Release Enhancing Agent<sup>†</sup> American Chemical Society 2000 methanesulfonylation functionalized Efficient DMP Functionalization cognition enhancer drug candidate 1 Pyridinylmethyl chlorination Enhancing anthracenone bisalkylation Bis Synthesi mesylate scale synthesis Release Acetylcholine novel alkylating agent 7 Agent hydrolysis anthrone process proceeds Fluoro 2000-10-21 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Efficient_Pyridinylmethyl_Functionalization_Synthesis_of_10_10-Bis_2-fluoro-4-pyridinyl_methyl_-9_10_i_H_i_-anthracenone_DMP_543_an_Acetylcholine_Release_Enhancing_Agent_sup_sup_/3711639 2-Fluoro-4-methylpyridine (<b>3</b>) is efficiently functionalized by chlorination, hydrolysis and methanesulfonylation into the novel alkylating agent <b>7</b>. This mesylate is used for the bisalkylation of anthrone under carefully defined conditions to prepare the cognition enhancer drug candidate <b>1</b>. This process proceeds in up to 37% overall yield and is adaptable for large scale synthesis.