6-bromo-2,1,3-benzoxadiazol-1-ium-1-olate -Drug Synthesis Database

【结构式】

【分子编号】59797

【品名】6-bromo-2,1,3-benzoxadiazol-1-ium-1-olate

【CA登记号】

【分子式】C₆H₃BrN₂O₂

【分子量】215.0061

【元素组成】C 33.52% H 1.41% Br 37.16% N 13.03% O 14.88%

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：(III)

The precursor benzofurazan boronic acid (V) was prepared as follows. Bromination of o-nitroaniline (I) by means of N-bromosuccinimide in AcOH afforded 4-bromo-2-nitroaniline (II). Treatment of (II) with NaOCl gave rise to the 5 bromobenzofurazan N-oxide (III), which was reduced to (IV) employing triphenylphosphine in boiling xylene. Then, lithiation of (IV), followed by reaction with triethyl borate furnished the target boronic acid (V).

参考文献中间体

合成目标

【1】 Hersperger, R.; Dawson, J.; Mueller, T.; Synthesis of 4-(8-benzo[1,2,5]oxadiazol-5-yl-[1,7]naphthyridine-6-yl)-benzoic acid: A potent and selective phosphodiesterase type 4D inhibitor. Bioorg Med Chem Lett 2002, 12, 2, 233.
【2】 Hersperger, R. (Novartis AG); Naphtyridine derivs.. EP 0934320; US 6136821; WO 9818796 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	11608	o-Nitroaniline; 2-Nitroaniline; 2-Nitrophenylamine	88-74-4	C₆H₆N₂O₂	详情	详情
(II)	59796	4-bromo-2-nitroaniline; 4-bromo-2-nitrophenylamine		C₆H₅BrN₂O₂	详情	详情
(III)	59797	6-bromo-2,1,3-benzoxadiazol-1-ium-1-olate		C₆H₃BrN₂O₂	详情	详情
(IV)	59798	5-bromo-2,1,3-benzoxadiazole		C₆H₃BrN₂O	详情	详情
(V)	59799	2,1,3-benzoxadiazol-5-ylboronic acid		C₆H₅BN₂O₃	详情	详情

Extended Information