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> Jaan A. Pesti George F. Huhn Jianguo Yin Yide Xing Joseph M. Fortunak Richard A. Earl 10.1021/jo9804339.s001 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. 2000-10-21 00:00:00 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