methyl 2-[4-(2-methyl-1H-indol-5-yl)phenyl]propanoate -Drug Synthesis Database

【结构式】

【分子编号】26398

【品名】methyl 2-[4-(2-methyl-1H-indol-5-yl)phenyl]propanoate

【CA登记号】

【分子式】C₁₉H₁₉NO₂

【分子量】293.3654

【元素组成】C 77.79% H 6.53% N 4.77% O 10.91%

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：(VI)

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.

参考文献中间体

合成目标

【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