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【结 构 式】

【分子编号】39638

【品名】2-[5-methoxy-2-methyl-1-(4-nitrobenzoyl)-1H-indol-3-yl]acetic acid

【CA登记号】

【 分 子 式 】C19H16N2O6

【 分 子 量 】368.34592

【元素组成】C 61.96% H 4.38% N 7.61% O 26.06%

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:(IV)

The condensation of methyl 5-methoxy-2-methylindole-3-acetate (I) with p-nitrobenzoyl chloride (II) by means of NaH in toluene gives methyl 1-(p-nItrobenzoyl)-5-methoxy-2-methylindole-3-acetate (III), which is hydrolyzed with p-toluenesulfonic acid in refluxing acetic acid yielding the corresponding free acid (IV). The reduction of (IV) with H2 over Pd/C in methanol affords 1-(p-aminobenzoyl)-5-methoxy-2-methyl indole-3-acetic acid (V) , which is finally treated with NaNO2 and HCl in acetic acid, and with NaN3 in water.

1 Tricerri, S.; et al.; Synthesis and preliminary pharmacological data on zidometacin, a new anti-inflammatory compound. Eur J Med Chem 1979, 14, 181-183.
2 Blancafort, P.; Serradell, M.N.; de Angelis, L.; Castaner, J.; Zidometacin. Drugs Fut 1979, 4, 11, 839.
3 Tricerri, S.; Bianchetti, A.; DE 2722399 .
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) 39636 methyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate C13H15NO3 详情 详情
(II) 18941 p-nitrobenzoyl chloride; 4-nitrobenzoyl chloride 122-04-3 C7H4ClNO3 详情 详情
(III) 39637 methyl 2-[5-methoxy-2-methyl-1-(4-nitrobenzoyl)-1H-indol-3-yl]acetate C20H18N2O6 详情 详情
(IV) 39638 2-[5-methoxy-2-methyl-1-(4-nitrobenzoyl)-1H-indol-3-yl]acetic acid C19H16N2O6 详情 详情
(V) 39639 2-[1-(4-aminobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid C19H18N2O4 详情 详情
Extended Information