5-bromo-2-pyridinecarbonitrile -Drug Synthesis Database

【结构式】

【分子编号】60321

【品名】5-bromo-2-pyridinecarbonitrile

【CA登记号】

【分子式】C₆H₃BrN₂

【分子量】183.0073

【元素组成】C 39.38% H 1.65% Br 43.66% N 15.31%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XII)

Treatment of 2,5-dibromopyridine (XI) with NaCN/CuCN gives rise to nitrile (XII). Cycloaddition of NaN3 to the cyano group of (XII) then leads to the tetrazolyl pyridine (XIII) (1). Further methylation of tetrazole (XIII) with iodomethane and KOH produces a mixture of methylated regioisomers (XIV) and (XV). The desired 2-methyl tetrazole derivative (XIV) is finally subjected to Stille coupling with the aryl stannane (X) to furnish the title compound

参考文献中间体

合成目标

【1】 Im, W.; Lee, T.; Cho, J.; Choi, S.; Rhee, J.; In vitro and in vivo studies of hetero-ring substituted pyridine containing oxazolidinone derivatives, including DA-7867. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-1311.
【2】 Lee, J.-G.; Lee, J.-J.; Park, S.-K.; Lee, T.-H.; Leem, W.-B.; Cho, J.-H.; Choi, S.-H.; Kim, D.-G.; Sung, H.-J. (Dong-A Pharmaceutical Co., Ltd.); Novel oxazolidinone derivs. and a process for the preparation thereof. WO 0194342 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(X)	60320	N-({3-[3-fluoro-4-(trimethylstannanyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide		C₁₅H₂₁FN₂O₃Sn	详情	详情
(XI)	19330	2,5-dibromopyridine	624-28-2	C₅H₃Br₂N	详情	详情
(XII)	60321	5-bromo-2-pyridinecarbonitrile		C₆H₃BrN₂	详情	详情
(XIII)	60322	5-bromo-2-(1H-1,2,3,4-tetraazol-5-yl)pyridine		C₆H₄BrN₅	详情	详情
(XIV)	60323	5-bromo-2-(1-methyl-1H-1,2,3,4-tetraazol-5-yl)pyridine		C₇H₆BrN₅	详情	详情
(XV)	60324	5-bromo-2-(2-methyl-2H-1,2,3,4-tetraazol-5-yl)pyridine		C₇H₆BrN₅	详情	详情

Extended Information