A practical synthesis of 2-((1H-pyrrolo[2,3-b]pyridine-4-yl)methylamino)-5-fluoronicotinic acid

被引：42

作者：

Wang, X ^{[1
]}

Zhi, B ^{[1
]}

Baum, J ^{[1
]}

Chen, Y ^{[1
]}

Crockett, R ^{[1
]}

Huang, L ^{[1
]}

Eisenberg, S ^{[1
]}

Ng, J ^{[1
]}

Larsen, R ^{[1
]}

Martinelli, M ^{[1
]}

Reider, P ^{[1
]}

机构：

[1] Amgen Inc, Chem Proc R&D, Thousand Oaks, CA 91320 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 10期

关键词：

D O I：

10.1021/jo0602571

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical synthesis of a key pharmaceutical intermediate, 2-[(1H-pyrrolo[2,3-b]pyridine-4-yl)methylamino]-5-fluoronicotinic acid ( 1), is described. To introduce the aminomethyl moiety of 2 via a palladium-catalyzed cyanation/reduction sequence, a regioselective chlorination of 7-azaindole via the N-oxide was developed. A highly selective monodechlorination of 2,6-dichloro-5-fluoronicotinic acid was discovered to afford the nicotinic acid 3. The two building blocks 2 and 3 were then coupled to complete the preparation of 1.

引用

页码：4021 / 4023

页数：3

共 26 条

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