Improved procedure for the preparation of 7-methoxy-2-methyl-1-(2-morpholinoethyl)-1H-indole-3-carboxylic acid, key intermediate in the synthesis of novel 3-amidoindole and indolopyridone cannabinoid ligands

被引：5

作者：

Zhao, Rulin ^{[1
]}

Wang, Bei ^{[1
]}

Wu, Hong ^{[1
]}

Hynes, John, Jr. ^{[1
]}

Leftheris, Katerina ^{[1
]}

Balasubramanian, Balu ^{[1
]}

Barrish, Joel C. ^{[1
]}

Chen, Bang-Chi ^{[1
]}

机构：

[1] Bristol Myers Squibb Res & Dev, Discovery Chem, Princeton, NJ 08543 USA

来源：

ARKIVOC | 2010年

关键词：

cannabinoid (CB2) receptor; synthesis; indole N-alkylation; indole-3-carboxylate; BIOLOGICAL EVALUATION; RECEPTOR; DERIVATIVES; ANALOGS; DESIGN; POTENT;

D O I：

10.3998/ark.5550190.0011.610

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new efficient method was developed for the preparation of 2-methyl-1-(2-morpholinoethyl)-1H-indole-3-carboxylic acid. The new method involves N-alkylation of 7-methoxy-2-methylindole with 4-(2-chloroethyl) morpholine hydrochloride followed by trichloroacetylation and hydrolysis in 3 steps and 88% overall yield.

引用

页码：89 / 95

页数：7

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