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【结 构 式】

【分子编号】51282

【品名】1-benzyl-1H-indol-5-ol

【CA登记号】

【 分 子 式 】C15H13NO

【 分 子 量 】223.27436

【元素组成】C 80.69% H 5.87% N 6.27% O 7.17%

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:(IV)

The N-benzyl indole derivative (III) was prepared by alkylation of 5-(benzyloxy)indole (I) with benzyl bromide (II) in the presence of KOH. The O-benzyl protecting group of (III) was subsequently removed by transfer hydrogenolysis with ammonium formate and Pd/C to afford the 5-hydroxyindole (IV), which was further condensed with 3-chloro-4-fluorobenzonitrile (V) to produce the diaryl ether (VI). Finally, basic hydrolysis of the cyano group of (VI) gave the corresponding benzoic acid.

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) 12912 1-(Bromomethyl)benzene; Alpha-bromotoluene 100-39-0 C7H7Br 详情 详情
(III) 51281 benzyl 1-benzyl-1H-indol-5-yl ether; 1-benzyl-5-(benzyloxy)-1H-indole C22H19NO 详情 详情
(IV) 51282 1-benzyl-1H-indol-5-ol C15H13NO 详情 详情
(V) 51277 3-Chloro-4-fluorobenzonitrile 117482-84-5 C7H3ClFN 详情 详情
(VI) 51283 4-[(1-benzyl-1H-indol-5-yl)oxy]-3-chlorobenzonitrile C22H15ClN2O 详情 详情
Extended Information