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【结 构 式】 
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【分子编号】59796 【品名】4-bromo-2-nitroaniline; 4-bromo-2-nitrophenylamine 【CA登记号】 |
【 分 子 式 】C6H5BrN2O2 【 分 子 量 】217.02198 【元素组成】C 33.21% H 2.32% Br 36.82% N 12.91% O 14.74% |
合成路线1
该中间体在本合成路线中的序号：(II)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).
| 【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 |
合成路线2
该中间体在本合成路线中的序号：(I)Acylation of 4-bromo-2-nitroaniline (I) with 5-chlorothiophene-2-sulfonyl chloride (II) in pyridine affords sulfonamide (III). The nitro group of (III) is then reduced to amine (IV) by means of hydrazine hydrate in the presence of Raney nickel. Further acylation of amine (IV) with sulfonyl chloride (II) furnishes the target bis-sulfonamide.
| 【1】 Cockerill, G.S.; et al.; Bis(sulfonamides) as inhibitors of aroB. Unsymmetrical sulfonamide substitution and diamine core SAR. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-739. |
| 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) | 59796 | 4-bromo-2-nitroaniline; 4-bromo-2-nitrophenylamine | C6H5BrN2O2 | 详情 | 详情 | |
| (II) | 61418 | 5-Chlorothiophene-2-sulfonyl chloride; 5-Chlorothiophene-2-sulfonyl chloride; 5-Chlorothiophene-2-sulphonyl chloride; 5-Chlorothiophene-2-sulphonyl chloride (Light & heat sensitive); 5-Chlorothiophene-2-sulphonylchloride; 5-Chlorothiophenesulphonyl chloride; 2,3-Dimethylthiophene | 2766-74-7 | C4H2Cl2O2S2 | 详情 | 详情 |
| (III) | 61419 | N-(4-bromo-2-nitrophenyl)-5-chloro-2-thiophenesulfonamide | C10H6BrClN2O4S2 | 详情 | 详情 | |
| (IV) | 61420 | N-(2-amino-4-bromophenyl)-5-chloro-2-thiophenesulfonamide | C10H8BrClN2O2S2 | 详情 | 详情 |