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【结 构 式】

【分子编号】32917

【品名】ethyl (Z)-2-azido-3-(3,5-dimethylphenyl)-2-propenoate

【CA登记号】

【 分 子 式 】C13H15N3O2

【 分 子 量 】245.28112

【元素组成】C 63.66% H 6.16% N 17.13% O 13.05%

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:(VIII)

The intermediate benzyl 5,7-dimethylindole-2-carboxylate (X) was prepared by several procedures. Diazotization of 2,4-dimethylaniline (I), followed by Japp-Klingemann condensation of the diazonium salt (II) with ethyl 2-methyl-3-oxobutyrate (III) furnished hydrazone (IV). Subsequent Fischer indole synthesis in formic acid at 75 C provided ethyl 5,7-dimethylindole-2-carboxylate (V). An alternative route to indole (V) involved condensation of 3,5-dimethylbenzaldehyde (VI) with ethyl azidoacetate (VII) in ethanolic NaOEt, followed by thermal cyclization of the resulting azidocinnamate ester (VIII). Basic hydrolysis of ethyl ester (V) gave carboxylic acid (IX), which was converted to the benzyl ester (X) upon treatment with benzyl bromide and DBU.

1 Brodin, R.; Boigegrain, R.; Molimard, J.-C.; Bignon, E.; Olliero, D. (Sanofi-Synthelabo ); Carboxamidothiazole derivs., preparation, pharmaceutical compsns. containing them. EP 1017693; FR 2768737; FR 2777887; WO 9915525 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
12912 1-(Bromomethyl)benzene; Alpha-bromotoluene 100-39-0 C7H7Br 详情 详情
(I) 32911 2,4-dimethylaniline; 2,4-dimethylphenylamine 95-68-1 C8H11N 详情 详情
(II) 32912 2,4-dimethylbenzenediazonium C8H9N2 详情 详情
(III) 10362 ethyl 2-methyl-3-oxobutanoate; ethyl 2-methylacetoacetate 609-14-3 C7H12O3 详情 详情
(IV) 32913 ethyl 2-[(Z)-2-(2,4-dimethylphenyl)hydrazono]propanoate C13H18N2O2 详情 详情
(V) 32914 ethyl 5,7-dimethyl-1H-indole-2-carboxylate C13H15NO2 详情 详情
(VI) 32915 3,5-dimethylbenzaldehyde 5779-95-3 C9H10O 详情 详情
(VII) 32916 ethyl 2-azidoacetate 637-81-0 C4H7N3O2 详情 详情
(VIII) 32917 ethyl (Z)-2-azido-3-(3,5-dimethylphenyl)-2-propenoate C13H15N3O2 详情 详情
(IX) 32918 5,7-dimethyl-1H-indole-2-carboxylic acid C11H11NO2 详情 详情
(X) 32919 benzyl 5,7-dimethyl-1H-indole-2-carboxylate C18H17NO2 详情 详情
Extended Information