[发明专利]一种1‑（3‑溴苯基）‑1H‑四氮唑的制备方法

说明书

技术领域

本发明属于药物中间体领域，特别涉及一种1-(3-溴苯基)-1H-四氮唑的制备方法。

背景技术

1-苯基-1H-四氮唑(I)及其衍生物是重要的药物合成中间体，在有机药物等的合成中发挥着重要的作用(Grandane,A.；Tanc,M.；Zalubovskis,R.；Supuran,C.T.Synthesis of 6- tetrazolyl-substituted sulfocoumarins acting as highly potent and selective inhibitors of the tumor- associated carbonic anhydrase isoforms IX and XII.Bioorganic&Medicinal Chemistry,2014,22(5):1522-1528.；Dong,S.；Pasternak,A.；Suzuki,T.；Gu,X.；Fu,Q.；Jiang,J.； Ding,F.X.；Tang,H.；Dejesus,R.K.Preparation of spirocyclic compounds useful as inhibitors of renal outer medullary potassium(ROMK)chanel.WO 2015096035,2015.；Kamenecka,T.M.； Burris,T..Preparation of small molecule LXR inverse agonists,WO 2014085453,2014)。

文献报道1-(3-溴苯基)-1H-四氮唑化合物(I)的合成方法主要为3-溴苯胺、原甲酸三甲酯和叠氮化钠在路易斯酸如三氟甲磺酸钇、三氯化铁或甲烷磺酸等的作用下发生化学反应得到。(Sharghi,H.；Ebrahimpourmoghaddam,S.；Doroodmand,M.M..Facile synthesis of 5-substituted-1H-tetrazoles and 1-substituted-1H-tetrazoles catalyzed by recyclable 4′-phenyl-2,2′:6′2′-terpyridine copper(II)complex immobilized onto activated multi-walled carbon nanotubes.Journal of Organometallic Chemistry,2013,738,41-48.Su,W.K.；Hong,Z.； Shan,W.G.；Zhang,X.X.A facile synthesis of 1-substituted-1H-1,2,3,4-tetrazoles catalyzed by ytterbium triflate hydrate.European Journal of Organic Chemistry,2006,2006(12):2723-2726. Darvish,F.；Khazraee,S.Habibi,D.；Nasrollahzadeh,M.；Kamali,T.A.Green synthesis of the 1- substituted 1H-1,2,3,4-tetrazoles by application of the Natrolite zeolite as a new and reusable heterogeneous catalyst.Green Chemistry,2011,13(12):3499-3504；Darvish,F.；Khazraee,S.FeCl₃catalyzed one pot synthesis of 1-substituted-1H-1,2,3,4-tetrazoles under solvent-free conditions. International Journal of Organic Chemistry,2015,5(2):75-80.)。除叠氮化钠外，也有文献报道使用三甲硅基叠氮进行环合反应制备1-苯基-1H-四氮唑及其衍生物(Aridoss,G.；Laali,K.K. Building heterocyclic systems with RC(OR)²⁺carbocations in recyclable bronsted acidic ionic liquids:facile synthesis of 1-substituted 1H-1,2,3,4-trtrazoles,benzazoles and other ring systems with CH(OEt)₃and EtC(OEt)₃in[EtNH₃][NO₃]and[PMIM(SO₃H)[OTf].European Journal of Organic Chemistry,2011,2011(15):2827-2835.)，但上述反应需要使用易爆炸和有毒的叠氮化钠，为安全生产带来隐患，因此，开发新的合成方法具有重要意义。