Synthesis of novel halopyridinylboronic acids and esters. Part 4: Halopyridin-2-yl-boronic acids and esters are stable, crystalline partners for classical Suzuki cross-coupling |
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Authors: | Alexandre BouillonJean-Charles Lancelot Jana Sopkova de Oliveira SantosValérie Collot Philipppe R BovySylvain Rault |
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Institution: | a Centre d'Etudes et de Recherche sur le Médicament de Normandie, UFR des Sciences Pharmaceutiques, 5, rue Vaubénard, 14032 Caen Cedex, France b Sanofi-Synthélabo Recherche, 10, rue des Carrières, 92500 Rueil-Malmaison, France |
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Abstract: | This paper describes some methods for the synthesis and the isolation of novel 5 or 6-halopyridin-2-yl-boronic acids and esters 3, 4, 7. These compounds are prepared via a regioselective halogen-metal exchange using n-butyllithium and subsequent quenching with triisopropylborate starting from appropriate 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 arylhalides and authorise a strategy to produce new pyridines libraries. |
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Keywords: | boronic acids lithiation cross-coupling reaction pyridine |
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