Highly regioselective Buchwald-Hartwig amination at C-2 of 2,4-dichloropyridine enabling a novel approach to 2,4-bisanilinopyridine (BAPyd) libraries

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• 作者：Rebecca J. Burton ; M ; y L. Crowther ; Neal J. Fazakerley ; Shaun M. Fillery ; Barry M. Hayter ; Jason G. Kettle ; Caroline A. McMillan ; Paula Perkins ; Peter Robins ; Peter M. Smith ; Emma J. Williams ; Gail L. Wrigley
• 关键词：GRIJQAVFXUJSOQ-UHFFFAOYSA-N ; ZMASOVJVBNDURA-UHFFFAOYSA-N ; CVYLMNRVLRLOHQ-UHFFFAOYSA-N ; OSMXMYGGOFVVBP-UHFFFAOYSA-N ; GHPPHGWZAXXQKD-UHFFFAOYSA-N ; WDLNJJAPZUTNMX-UHFFFAOYSA-N ; NNTZSTAMOYFESP-UHFFFAOYSA-N ; XOTCPBULDLVLLM-UHFFFAOYSA-N ; REAGPDVETOXYHD-UHFFFAOYSA-N ; UCWPFHAFXAGKLZ-UHFFFAOYSA-N ; VCVJCCFYBCAAKN-UHFFFAOYSA-N ; AGYIDINAMUREIM-UHFFFAOYSA-N ; CMNMBPXCCUBUTM-UHFFFAOYSA-N ; IMZZTSRIDXDVEN-UHFFFAOYSA-N ; JWBCYDLYDYBKHA-UHFFFAOYSA-N ; TWXMCJPUZKIFKI-UHFFFAOYSA-N ; JYLUAQLCIFEIAV-UHFFFAOYSA-N ; BMTOXWA
• 刊名：Tetrahedron Letters
• 出版年：11 December, 2013
• 年：2013
• 卷：54
• 期：50
• 页码：6900-6904
• 全文大小：1907 K

文摘

The highly regioselective Buchwald-Hartwig amination at C-2 of the cheap and readily accessible reagent, 2,4-dichloropyridine with a range of anilines and heterocyclic amines is described. This new methodology is robust and provides a facile access to 4-chloro-N-phenylpyridin-2-amines on 0.25 mol scale. These intermediates undergo a further Buchwald-Hartwig amination at higher temperature to enable rapid exploration of the chemical space at C-4 and to provide a library of 2,4-bisaminopyridines.