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【结 构 式】

【分子编号】27750

【品名】Indole-2-carboxylic acid methyl ester; 1H-indole-2-carboxylic acid methyl ester

【CA登记号】1202-04-6

【 分 子 式 】C10H9NO2

【 分 子 量 】175.187

【元素组成】C 68.56% H 5.18% N 8% O 18.27%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(II)

2-Indolecarboxylic acid (I) was esterified with MeOH and SOCl2 to provide methyl ester (II). Subsequent N-alkylation of (II) using methyl iodide and NaH afforded N-methyl indole (III). Guanidine, liberated by treatment of the hydrochloride salt with NaOMe, was finally condensed with indole ester (III) at 130 C to produce the corresponding acylguanidine, which was isolated as the mesylate salt.

1 Kojima, A.; Kitano, M.; Miyagishi, A.; Noguchi, T.; Yagi, H.; Nakano, K.; Ohashi, N. (Sumitomo Pharmaceuticals Co., Ltd.); Indoloylguanidine derivs. as inhibitors of sodium-hydrogen exchange. CA 2121391; EP 0622356; JP 1995010839 .
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) 25226 1H-Indole-2-carboxylic acid; Indole-2-carboxylic acid 1477-50-5 C9H7NO2 详情 详情
(II) 27750 Indole-2-carboxylic acid methyl ester; 1H-indole-2-carboxylic acid methyl ester 1202-04-6 C10H9NO2 详情 详情
(III) 27751 methyl 1-methyl-1H-indole-2-carboxylate C11H11NO2 详情 详情
(IV) 14790 Guanidine 113-00-8 CH5N3 详情 详情

合成路线2

该中间体在本合成路线中的序号:(I)

The alkylation of 1H-indole-2-carboxylic acid methyl ester (I) with 2-phenylethyl bromide (II) by means of NaH in DMF gives 1-(2-phenylethyl)-1H-indole-2-carboxylic acid methyl ester (II), with is hydrolyzed with NaOH in methanol/water yielding the corresponding free acid (IV). Finally, this compound is condensed with guanidine by means of CDI and TEA in THF/DMF.

1 Kitano, M.; Miyagishi, A.; Ohashi, N.; Noguchi, T.; Nakano, K.; Kojima, A.; Synthesis and biological activity of N-(aminoiminomethyl)-1H-indole carboxamide derivatives as Na+/H+ exchanger inhibitors. Chem Pharm Bull 1999, 47, 11, 1538.
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) 27750 Indole-2-carboxylic acid methyl ester; 1H-indole-2-carboxylic acid methyl ester 1202-04-6 C10H9NO2 详情 详情
(II) 20730 1-(2-bromoethyl)benzene;1-Bromo-2-phenylethane;(2-Bromoethyl)benzene;Phenethyl bromide 103-63-9 C8H9Br 详情 详情
(III) 40402 methyl 1-phenethyl-1H-indole-2-carboxylate C18H17NO2 详情 详情
(IV) 40403 1-phenethyl-1H-indole-2-carboxylic acid C17H15NO2 详情 详情
(V) 14790 Guanidine 113-00-8 CH5N3 详情 详情
Extended Information