Direct synthesis of Cbz-protected (2-amino)-6-(2-aminoethyl)pyridines

被引：5

作者：

Roy, Sudipta ^{[1
]}

Zych, Andrew J. ^{[1
]}

Herr, R. Jason ^{[1
]}

Cheng, Cliff ^{[2
]}

Shipps, Gerald W., Jr. ^{[2
]}

机构：

[1] AMRI, Dept Med Chem, Albany, NY 12212 USA

[2] Schering Plough Res Inst, Cambridge, MA 02141 USA

来源：

TETRAHEDRON | 2010年 / 66卷 / 11期

关键词：

2-(Aminoethyl)pyridines; Aminoethylation; Suzuki-Miyaura reactions; Pd-catalyzed reactions; 2-Halopyridines; HIV-1; REVERSE-TRANSCRIPTASE; ACTIVE HYDROGEN COMPOUNDS; CROSS-COUPLING REACTIONS; ASYMMETRIC-SYNTHESIS; NUCLEOPHILIC-SUBSTITUTION; DESIGN; SUZUKI; PYRIDYLETHYLATION; DERIVATIVES; INHIBITORS;

D O I：

10.1016/j.tet.2010.01.025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel series of (2-amino)-6-(2-aminoethyl)pyridines were prepared by a convenient Suzuki-Miyaura coupling approach from 2-amino-6-bromopyridines. Benzyl vinylcarbamate was first treated with 9-BBN followed by aqueous NaOH and then the appropriate bromopyridine precursors were added into the mixture. The mixture was finally heated in presence of a palladium catalyst to provide the corresponding products in overall high yields. The procedure is extended to the preparation of related pyrazine and pyrimidine compounds as well as (2-amido)- and (2-alkoxy)-6-(2-aminoethyl)pyridines. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1973 / 1979

页数：7

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