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【结 构 式】

【分子编号】51275

【品名】ethyl 5-(benzyloxy)-1H-indole-1-carboxylate

【CA登记号】

【 分 子 式 】C18H17NO3

【 分 子 量 】295.33792

【元素组成】C 73.2% H 5.8% N 4.74% O 16.25%

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:(II)

The acylation of 5-(benzyloxy)indole (I) with ethyl chloroformate produced the N-(ethoxycarbonyl)indole (II), which was debenzylated by transfer hydrogenolysis with ammonium formate in the presence of Pd/C to afford the 5-hydroxyindole (III). Condensation of (III) with 3-chloro-4-fluorobenzonitrile (IV) produced the diaryl ether (V). Then, basic hydrolysis of the cyano and ethoxycarbonyl groups of (V) gave the benzoic acid derivative (VI). Finally, N-alkylation of the indole ring of (VI) with 4-phenoxybenzyl bromide (VII) furnished the title compound.

1 Mase, T.; Inami, H.; Hara, H.; Fujii, M; Oritani, H.; Koutoku, H.; Igarashi, S.; A novel class of inhibitors for human steroid 5alpha-reductase: Synthesis and biological evaluation of indole derivatives. II. Chem Pharm Bull 2000, 48, 3, 382.
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) 30840 5-Benzyloxyindole; benzyl 1H-indol-5-yl ether; 5-(benzyloxy)-1H-indole 1215-59-4 C15H13NO 详情 详情
(II) 51275 ethyl 5-(benzyloxy)-1H-indole-1-carboxylate C18H17NO3 详情 详情
(III) 51276 ethyl 5-hydroxy-1H-indole-1-carboxylate C11H11NO3 详情 详情
(IV) 51277 3-Chloro-4-fluorobenzonitrile 117482-84-5 C7H3ClFN 详情 详情
(V) 51278 ethyl 5-(2-chloro-4-cyanophenoxy)-1H-indole-1-carboxylate C18H13ClN2O3 详情 详情
(VI) 51279 3-chloro-4-(1H-indol-5-yloxy)benzoic acid C15H10ClNO3 详情 详情
(VII) 51280 1-(bromomethyl)-4-phenoxybenzene; 4-(bromomethyl)phenyl phenyl ether C13H11BrO 详情 详情
Extended Information