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【结 构 式】 
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【分子编号】51277 【品名】3-Chloro-4-fluorobenzonitrile 【CA登记号】117482-84-5 |
【 分 子 式 】C7H3ClFN 【 分 子 量 】155.5586632 【元素组成】C 54.05% H 1.94% Cl 22.79% F 12.21% N 9% |
合成路线1
该中间体在本合成路线中的序号：(V)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 |
合成路线2
该中间体在本合成路线中的序号：(IV)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 |