用于平行合成O-芳氧基胺的氟代标记的N-羟基邻苯二甲酰亚胺。

Fluorous tagged N-hydroxy phthalimide for the parallel synthesis of O-aryloxyamines.

作者信息

Gaucher-Wieczorek Florence S, Maillard Ludovic T, Badet Bernard, Durand Philippe

机构信息

Centre de recherches de Gif, Institut de Chimie des Substances Naturelles, UPR 2301-CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.

出版信息

J Comb Chem. 2010 Sep 13;12(5):655-8. doi: 10.1021/cc100098v.

DOI:10.1021/cc100098v

PMID:20831264

Abstract

The parallel synthesis of O-aryloxyamines remains an unfulfilled need in the field of medicinal chemistry and fragment-based approaches. To fill this gap a solution-phase two-step process based on (1) a copper-catalyzed cross-coupling of aryl boronic acids with a fluorous tagged N-hydroxyphthalimide, and (2) a supported aminolysis was designed and optimized using Taguchi's method. A library of O-aryloxyamines was synthesized in high yields with high purity and diversity.

摘要

在药物化学和基于片段的方法领域，O-芳氧基胺的平行合成仍然是一个未得到满足的需求。为了填补这一空白，设计并使用田口方法优化了一种基于（1）芳基硼酸与氟代标记的N-羟基邻苯二甲酰亚胺的铜催化交叉偶联以及（2）负载型氨解的溶液相两步法。以高收率、高纯度和多样性合成了一个O-芳氧基胺库。