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【结 构 式】 
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【分子编号】26397 【品名】methyl 2-[4-[2-methyl-3-(phenylsulfanyl)-1H-indol-5-yl]phenyl]propanoate 【CA登记号】 |
【 分 子 式 】C25H23NO2S 【 分 子 量 】401.52916 【元素组成】C 74.78% H 5.77% N 3.49% O 7.97% S 7.99% |
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：(V)The cyclization of 4-iodoaniline (I) with 1-(phenylsulfanyl)acetone (II) by means of tert-butyl hypochlorite in dichloromethane gives the iodoindole (III), which is condensed with the phenylboronic ester (IV) using a Pd catalyst in DMSO to yield 2-[4-[2-methyl-3-(phenylsulfanyl)-1H-indol-5-yl]phenyl]propionic acid methyl ester (V). The desulfurization of (V) with thiosalicylic acid in hot TFA affords 2-[4-(2-methyl-1H-indol-5-yl)phenyl]propionic acid methyl ester (VI), which is finally hydrolyzed with LiOH in THF/methanol/water.
| 【1】 Black, C.; Leger, S.; Bayly, C.I.; Ouimet, N.; Ouellet, M.; Percival, D. (Merck Frosst Canada Inc.); Biaryl-acetic acid derivs. and their use as COX-2 inhibitors. US 5994379; WO 9941224 . |
| 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) | 26393 | 4-iodoaniline; 4-iodophenylamine | 540-37-4 | C6H6IN | 详情 | 详情 |
| (II) | 26394 | 1-(phenylsulfanyl)acetone | 1435-53-6 | C9H10OS | 详情 | 详情 |
| (III) | 26395 | 5-iodo-2-methyl-1H-indol-3-yl phenyl sulfide; 5-iodo-2-methyl-3-(phenylsulfanyl)-1H-indole | C15H12INS | 详情 | 详情 | |
| (IV) | 26396 | methyl 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate | C16H23BO4 | 详情 | 详情 | |
| (V) | 26397 | methyl 2-[4-[2-methyl-3-(phenylsulfanyl)-1H-indol-5-yl]phenyl]propanoate | C25H23NO2S | 详情 | 详情 | |
| (VI) | 26398 | methyl 2-[4-(2-methyl-1H-indol-5-yl)phenyl]propanoate | C19H19NO2 | 详情 | 详情 |
Extended Information