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【结 构 式】

【分子编号】18795

【品名】methyl 2-(1H-indol-1-yl)acetate

【CA登记号】

【 分 子 式 】C11H11NO2

【 分 子 量 】189.21388

【元素组成】C 69.83% H 5.86% N 7.4% O 16.91%

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:(II)

The target compound was obtained by several related ways. Indolylethanol (III) was either prepared by alkylation of indole (I) with methyl bromoacetate, followed by reduction of the resulting indolylacetate (II) with LiAlH4 or by alkylation of (I) with 2-bromoethanol. Alkylation of (III) with 4-fluorobenzaldehyde (IV) in the presence of NaH or condensation with 4-hydroxybenzaldehyde (V) under Mitsunobu conditions provided ether (VII). Alternatively, (VII) was prepared by alkylation of indole (I) with 4-(bromoethoxy)benzaldehyde (VI). Then, Knoevenagel condensation of aldehyde (VII) with 2,4-thiazolidinedione (VIII) in the presence of piperidinium benzoate in refluxing toluene with azeotropic removal of water yielded benzylidene compound (IX). Reduction of the olefinic double bond by either hydrogenation in the presence of an excess of Pd/C or by chemical reduction with Mg in MeOH provided the target benzyl compound. Alternatively, indolylethanol (III) was condensed with hydroxybenzyl compound (X) in the presence of tributyl phosphine and 1,1'-(azodicarbonyl)dipiperidine (ADDP) in benzene to give (XI), which was finally deprotected by hydrogenation in the presence of an excess of Pd/C in dioxan.

1 Lohray, B.B.; et al.; Novel indole containing thiazolidinedione derivatives as potent euglycemic and hypolipidaemic agents. Bioorg Med Chem Lett 1997, 7, 7, 785.
2 Rao, K.N.; Reddy, A.K.; Reddy, P.G.; Vikramadityan, R.K.; Madhavan, G.R.; Bhushan, V.; Rajagopolan, R.; Mamidi, R.N.V.S.; Rajesh, B.M.; Jajoo, H.K.; Rao, B.P.; Murali, N.; Chakrabarti, R.; Subramaniam, S.; Lohray, B.B.; Novel euglycemic and hypolipidemic agent. J Med Chem 1998, 41, 10, 1619.
3 Fujita, T.; Fujimoto, K.; Yoshioka, T.; Yanagisawa, H.; Fujiwara, T.; Horikoshi, H.; Oguchi, M.; Wada, K. (Sankyo Co., Ltd.); Heterocyclic cpds. having antidiabetic activity, their preparation and their use. CA 2146701; EP 0676398; JP 1995330728; US 5624935; US 5834501; US 5962470; US 6117893 .
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) 15292 Indole; 1H-indole 120-72-9 C8H7N 详情 详情
(II) 18795 methyl 2-(1H-indol-1-yl)acetate C11H11NO2 详情 详情
(III) 18796 2-(1H-indol-1-yl)-1-ethanol C10H11NO 详情 详情
(IV) 12337 4-fluorobenzaldehyde 459-57-4 C7H5FO 详情 详情
(V) 13433 4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde 123-08-0 C7H6O2 详情 详情
(VI) 18799 4-(2-bromoethoxy)benzaldehyde 52191-15-8 C9H9BrO2 详情 详情
(VII) 18800 4-[2-(1H-indol-1-yl)ethoxy]benzaldehyde C17H15NO2 详情 详情
(VIII) 10883 1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione 2295-31-0 C3H3NO2S 详情 详情
(IX) 18802 5-((E)-[4-[2-(1H-indol-1-yl)ethoxy]phenyl]methylidene)-1,3-thiazolidine-2,4-dione C20H16N2O3S 详情 详情
(X) 18803 5-(4-hydroxybenzyl)-3-trityl-1,3-thiazolidine-2,4-dione C29H23NO3S 详情 详情
(XI) 18804 5-[4-[2-(1H-indol-1-yl)ethoxy]benzyl]-3-trityl-1,3-thiazolidine-2,4-dione C39H32N2O3S 详情 详情
Extended Information