N-烷基-1H-吡唑[3,4-b]并吡啶类衍生物的合成

Synthesis of N-Alkyl-1H-Pyrazolo[3,4-b]pyridine Derivatives

摘要: 根据文献中对7-氮杂吲哚N-H烷基化取代的方法报道，参照其合成路线，设计并合成了一系列未见文献报道的N-烷基-1H-吡唑[3,4-b]并吡啶化合物，并对1H-吡唑[3,4-b]并吡啶N-H烷基取代的反应条件进行优化改进。实验以1H-吡唑[3,4-b]并吡啶为起始原料，N,N-二甲基甲酰胺为溶剂，4-二甲氨基吡啶做催化剂，冰浴条件下以氢化钠为脱氢试剂30 min，室温条件下加入不同的溴代烷烃进行取代30 min，在惰性气体保护下进行。结果表明在此条件下生成目标产物效果最佳，收率在90%~94%之间。化合物结构经过核磁氢谱、核磁碳谱以及质谱的联合验证；该方法具有操作简单、反应时间较短、条件温和、收率较高的特点。

Abstract: According to the reports on the N-H alkylation substitution of 7-azaindole in the literature and referring to its synthetic route, a series of N-alkyl-1H-pyrazolo[3,4-b] pyridine compound were designed and synthesized, and the reaction conditions of 1H-pyrazolo[3,4-b] pyridine N-H alkyl substitution were optimized and improved. In the experiment, 1H-pyrazo[3,4-b]pyridine was used as the starting material, N,N-dimethylformamide was used as the solvent, 4-dimethylaminopyridine was used as the catalyst, and sodium hydride was used as the dehydration agent under ice bath conditions, hydrogen reagent for 30 min, different brominated alkanes were added for substitution at room temperature for 30 min, under the protection of inert gas. The results showed that the target product was the best under this condition, and the yield was between 90%~94%. The structure of the compound has been verified by H NMR, C NMR and mass spectrometry; the method has the characteristics of simple operation, short reaction time, mild conditions and high yield.