Synthesis of novel halopyridinylboronic acids and esters. Part 3: 2, or 3-halopyridin-4-yl-boronic acids and esters

被引:59
作者
Bouillon, A
Lancelot, JC
Collot, V
Bovy, PR
Rault, S
机构
[1] UFR Sci Pharmaceut, Ctr Etud Rech Medicament Normandie, F-14032 Caen, France
[2] Sanofi Synthelabo Rech, F-92500 Rueil Malmaison, France
关键词
halopyridin; boronic acid; boronic ester;
D O I
10.1016/S0040-4020(02)00416-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This paper describes a general method for the synthesis and the isolation of novel 2, or 3-halopyridin-4-yl-boronic acids and esters 12-14, 18-20. These compounds are prepared taking in account a regioselective halogen-metal exchange using nBuLi or directed ortho-metalation using LDA and subsequent quenching with triisopropylborate starting from appropriate mono or dihalopyridines. All substrates studied to date provided a single regioisomeric boronic acid or ester product. Additionally, these compounds have been found to undergo Pd-catalysed coupling with a range of arylhalides and authorise a strategy to produce new pyridines libraries. (C) 2002 Elsevier Science Ltd. All tights reserved.
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收藏
页码:4369 / 4373
页数:5
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