Department of Chemistry, CZ Openscreen , Masaryk University , Kamenice 5 , 625 00 Brno , Czech Republic.
International Clinical Research Center , St. Anne's University Hospital Brno , Pekařská 53 , 656 91 Brno , Czech Republic.
J Org Chem. 2018 Dec 21;83(24):15380-15405. doi: 10.1021/acs.joc.8b02655. Epub 2018 Dec 6.
3,4-Substituted-5-aminopyrazoles and 4-substituted-2-aminothiazoles are frequently used intermediates in medicinal chemistry and drug discovery projects. We report an expedient flexible synthesis of 3,4-substituted-5-aminopyrazoles (35 examples), based on palladium-mediated α-arylation of β-ketonitriles with aryl bromides. A library of 4-substituted-2-aminothiazoles (21 examples) was assembled by a sequence employing Suzuki coupling of newly prepared, properly protected pinacol ester and MIDA ester of 4-boronic acid-2-aminothiazole with (hetero)aryl halides.
3,4-取代-5-氨基吡唑和 4-取代-2-氨基噻唑是药物化学和药物发现项目中常用的中间体。我们报告了一种基于钯介导的β-酮腈与芳基溴化物的α-芳基化反应的灵活合成 3,4-取代-5-氨基吡唑（35 个实例）的方法。通过采用新制备的、适当保护的频哪醇酯与 4-硼酸-2-氨基噻唑的 MIDA 酯与（杂）芳基卤化物的 Suzuki 偶联反应，合成了 4-取代-2-氨基噻唑文库（21 个实例）。
