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【结 构 式】

【分子编号】26396

【品名】methyl 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate

【CA登记号】

【 分 子 式 】C16H23BO4

【 分 子 量 】290.16722

【元素组成】C 66.23% H 7.99% B 3.73% O 22.06%

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 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