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【结 构 式】

【分子编号】15298

【品名】4-[3-(3-aminobenzoyl)-1H-indol-1-yl]butyric acid

【CA登记号】

【 分 子 式 】C19H18N2O3

【 分 子 量 】322.3636

【元素组成】C 70.79% H 5.63% N 8.69% O 14.89%

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:(VII)

The Friedel-Crafts condensation of indole (I) with 3-nitrobenzoyl chloride (II) by means of AlCl3 in dichloromethane gives 3-(3-nitrobenzoyl)indole (III), which is allowed to react with ethyl 4-bromobutyrate (IV) by means of K2CO3 in DMF to yield 4-[3-(3-nitrobenzoyl)indol-1-yl]butyric acid ethyl ester (V). The hydrolysis of (V) with NaOH in dioxane/water affords the corresponding butyric acid (VI), which is hydrogenated with H2 over Pd/C in methanol/dioxane yielding 3-[3-(3-aminobenzoyl)indol-1-yl]butyric acid (VII). Finally, this compound is condensed with bis(4-isobutylphenyl)chloromethane (VIII) by means of ethyldiisopropylamine in dichloromethane.

1 Mealy, N.; Castaner, J.; FK-143. Drugs Fut 1996, 21, 5, 473.
2 Golden, P.; Hashimoto, M.; Tanaka, H.; Sawada, Y.; Okada, S.; Sawada, K.; Kayakiri, N.; 4-(1-Benzoylindol-3-yl)butyric acids and FK143: Novel nonsteroidal inhibitors of steroid 5alpha-reductase (II). Chem Pharm Bull 1999, 47, 4, 481.
3 Okada, S.; Sawada, K.; Kayakiri, N.; Saitoh, Y.; Tanaka, H.; Hashimoto, M. (Fujisawa Pharmaceutical Co., Ltd.); Indole derivs. EP 0458207; JP 1992244061; US 5212320; US 5312829 .
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) 15292 Indole; 1H-indole 120-72-9 C8H7N 详情 详情
(II) 15293 3-nitrobenzoyl chloride; m-nitrobenzoyl chloride 121-90-4 C7H4ClNO3 详情 详情
(III) 15294 1H-indol-3-yl(3-nitrophenyl)methanone C15H10N2O3 详情 详情
(IV) 11263 ethyl 4-bromobutanoate; Ethyl 4-bromobutyrate 2969-81-5 C6H11BrO2 详情 详情
(V) 15296 ethyl 4-[3-(3-nitrobenzoyl)-1H-indol-1-yl]butanoate C21H20N2O5 详情 详情
(VI) 15297 4-[3-(3-nitrobenzoyl)-1H-indol-1-yl]butyric acid C19H16N2O5 详情 详情
(VII) 15298 4-[3-(3-aminobenzoyl)-1H-indol-1-yl]butyric acid C19H18N2O3 详情 详情
(VIII) 15299 1-[chloro(4-isobutylphenyl)methyl]-4-isobutylbenzene C21H27Cl 详情 详情
Extended Information