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