A series of novel ‘drug-like’ small molecules based on 1H-benzo[d]imidazole derivatives bearing furan-2-yl, 4-piperidine and 5-aryl/aminoaryl substitutions were designed and synthesised. The key intermediate tert-butyl-4-(5-bromo-2-(furan-2-yl)-1H-benzo[d]imidazol-1-yl)piperidine-1-carboxylate (5) was synthesised via sequential reaction starting from 4-bromo-1-fluoro-2-nitrobenzene (1). The 5-aryl-substituted molecular library was generated via Suzuki–Miyura coupling of tert-butyl-4-(5-bromo-2-(furan-2-yl)-1H-benzo[d]imidazol-1-yl)piperidine-1-carboxylate (5) with various boronic acids while Buchwald coupling of 5 with various anilines generated the second molecular library of tert-butyl-4-(2-(furan-2-yl)-5-(arylamino)-1H-benzo[d]imidazol-1-yl)piperidine-1-carboxylates. The structures of all the newly synthesised compounds were confirmed by spectral analysis. The optimised procedure gives easy access to two new molecular libraries of 1H-benzo[d]imidazoles with operational simplicity and good yield.

设计并合成了一系列基于具有呋喃-2-基、4-哌啶和5-芳基/氨基芳基取代的1 H-苯并[ d ]咪唑衍生物的新型“类药物”小分子。采用序贯反应合成关键中间体叔丁基-4-(5-溴-2-(呋喃-2-基)-1 H-苯并[ d ]咪唑-1-基)哌啶-1-羧酸酯( 5 )从 4-溴-1-氟-2-硝基苯 ( 1 ) 开始。5-芳基取代分子库是通过 Suzuki-Miyura 偶联叔丁基-4-(5-溴-2-(呋喃-2-基)-1 H-苯并[ d ]咪唑-1-基)生成的哌啶-1-羧酸盐 ( 5) 与各种硼酸，而5与各种苯胺的 Buchwald 偶联产生叔丁基-4-(2-(呋喃-2-基)-5-(芳氨基)-1 H-苯并[ d ]咪唑的第二个分子库-1-基）哌啶-1-羧酸盐。所有新合成的化合物的结构都通过光谱分析得到证实。优化的程序可以轻松访问两个新的 1 H-苯并[ d ]咪唑分子库，操作简单，产率高。