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【结 构 式】 
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【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% |
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 |