4-(2-氯-4-氟苯基)-5-乙烯基哒嗪的合成  

Synthesis of 4-(2-chloro-4-fluorophenyl)-5-vinylpyridazine

作　　者：白东琴 赵梁悦 宋时洁 揣虹嫣 仝红娟 BAI Dong-qin;ZHAO Liang-yue;SONG Shi-jie;CHUAI Hong-yan;TONG Hong-juan(School of Pharmacy,Shaanxi Institute of International Trade&Commerce,Xianyang 712046,China;Xianyang Key Laboratory of Molecular Imaging and Drug Synthesis,Xianyang 712046,China)

机构地区：[1]陕西国际商贸学院医药学院,陕西咸阳712046 [2]咸阳市分子影像与药物合成重点实验室,陕西咸阳712046

出　　处：《精细与专用化学品》2024年第1期44-46,共3页Fine and Specialty Chemicals

基　　金：陕西省大学生创新创业训练计划项目(S202313123051)。

摘　　要：以5-(2,4-二氟苯基)哒嗪-4-胺为主要原料,经过Sandmeyer反应得到中间体4-(2,4-二氟苯基)-5-碘代哒嗪,4-(2,4-二氟苯基)-5-碘代哒嗪和乙烯基硼酸频哪醇酯发生Suzuki偶联反应得到目标化合物4-(2-氯-4-氟苯基)-5-乙烯基哒嗪。产物及中间体结构经核磁共振氢谱(~1HNMR)和电喷雾质谱(ESI-MS)表征。考察了反应物料比、催化剂种类以及反应温度对Suzuki偶联反应收率的影响,确定适宜的Suzuki偶联反应条件为:n(乙烯基硼酸频哪醇酯)∶n(4-(2,4-二氟苯基)-5-碘代哒嗪)=1.6∶1,反应温度为100℃,反应时间为5h。在该条件下,目标化合物的收率为61.7%(以4-(2,4-二氟苯基)-5-碘代哒嗪计)。4-(2-Chloro-4-fluorophenyl)-5-vinylpyridazine was synthesized from 5-(2,4-difluorophenyl)pyridazine-4-amine by Sandmeyer and Suzuki coupling reaction.The structures of the product and intermediate were characterized by 1 HNMR and ESI-MS.The effects of material ratio,catalyst type and reaction temperature on the yield of Suzuki cross-coupling reaction were also investigated.The suitable conditions for the Suzuki crosscoupling reaction were found as follows:The ratio of n(vinylborate):n(4-(2,4-difluorophenyl)-5-iodopyridazine)=1.6:1,the reaction temperature was 100℃,the reaction time was 5h,the yield of the target compound was up to 61.7%by this reaction conditions.

关 键 词：哒嗪衍生物 SUZUKI偶联反应 反应条件 

分 类 号：TQ463[化学工程—制药化工]