Efficient Pyridinylmethyl Functionalization: Synthesis of 10,10-Bis[(2-fluoro-4-pyridinyl)methyl]-9(10H)-anthracenone (DMP 543), an Acetylcholine Release Enhancing Agent

2-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 proc...

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Veröffentlicht in:	Journal of organic chemistry 2000-11, Vol.65 (23), p.7718-7722
Hauptverfasser:	Pesti, Jaan A, Huhn, George F, Yin, Jianguo, Xing, Yide, Fortunak, Joseph M, Earl, Richard A
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetylcholine - metabolism Alzheimer Disease - drug therapy Anthracenes - chemical synthesis Anthracenes - pharmacology Humans
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container_title	Journal of organic chemistry
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creator	Pesti, Jaan A Huhn, George F Yin, Jianguo Xing, Yide Fortunak, Joseph M Earl, Richard A
description	2-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.
doi_str_mv	10.1021/jo9804339
format	Article
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subjects	Acetylcholine - metabolism Alzheimer Disease - drug therapy Anthracenes - chemical synthesis Anthracenes - pharmacology Humans
title	Efficient Pyridinylmethyl Functionalization: Synthesis of 10,10-Bis[(2-fluoro-4-pyridinyl)methyl]-9(10H)-anthracenone (DMP 543), an Acetylcholine Release Enhancing Agent
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