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.