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【结 构 式】 
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【分子编号】68451 【品名】2-bromo-3-methoxyaniline 【CA登记号】 |
【 分 子 式 】C7H8BrNO 【 分 子 量 】202.05066 【元素组成】C 41.61% H 3.99% Br 39.55% N 6.93% O 7.92% |
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：(XXIX)Sandmeyer reaction of 2-amino-3-nitrophenol (XXVI) using NaNO2 and HBr in the presence of CuBr in H2O/dioxane gives 2-bromo-3-nitrophenol (XXVII), which by O-alkylation with MeI in the presence of Cs2CO3 in DMF affords the methyl ether (XXVIII). Subsequent reduction of the nitro derivative (XXVIII) with Fe powder in refluxing AcOH/EtOH provides 2-bromo-3-methoxyaniline (XXIX) . Addition of aniline (XXIX) to dimethyl acetylene dicarboxylate (XXX) in refluxing MeOH produces the amino diester (XXXI), which by cyclization at 240 °C in diphenyl ether affords the quinoline (X) .
| 【1】 Llinas-Brunet, M., Bailey, M.D., Goudreau, N. et al. Discovery of a potent and selective noncovalent linear inhibitor of the hepatitis C virus NS3 protease (BI 201335). J Med Chem 2010, 53(17): 6466-76. |
| 【2】 Llinas-Brunet, M., Bailey, M., Bhardwaj, P. et al. (Boehringer Ingelheim International GmbH & Co. KG). Hepatitis C inhibitor compounds. US 7585845. |
| 【3】 Bhardwaj, P., Forgione, P., Goudreau, N. et al. (Boehringer Ingelheim International GmbH). Hepatitis C inhibitor compounds. EP 1654261, JP 2006528937, JP 2010043129, US 2005020503, US 2011177030, US 8067438, WO 2004103996. |
| 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) | 68434 | methyl 8-bromo-4-hydroxy-7-methoxyquinoline-2-carboxylate | C12H10BrNO4 | 详情 | 详情 | |
| (XXVI) | 41985 | 2-amino-3-nitrophenol | 603-85-0 | C6H6N2O3 | 详情 | 详情 |
| (XXVII) | 68448 | 2-bromo-3-nitrophenol | 101935-40-4 | C6H4BrNO3 | 详情 | 详情 |
| (XXVIII) | 68449 | 2-bromo-1-methoxy-3-nitrobenzene;2-Bromo-3-nitroanisole | 67853-37-6 | C7H6BrNO3 | 详情 | 详情 |
| (XXIX) | 68451 | 2-bromo-3-methoxyaniline | C7H8BrNO | 详情 | 详情 | |
| (XXX) | 24551 | Dimethyl acetylenedicarboxylate; Dimethyl 2-butynedioate;Acetylenedicarboxylic acid dimethyl ester | 762-42-5 | C6H6O4 | 详情 | 详情 |
| (XXXI) | 68450 | dimethyl 2-((2-bromo-3-methoxyphenyl)amino)maleate | C13H14BrNO5 | 详情 | 详情 |
Extended Information