Practical application of new catalytic methods: a concise synthesis of a potent PDE IV inhibitor

被引：29

作者：

Albaneze-Walker, J ^{[1
]}

Murry, JA ^{[1
]}

Soheili, A ^{[1
]}

Ceglia, S ^{[1
]}

Springfield, SA ^{[1
]}

Bazaral, C ^{[1
]}

Dormer, PG ^{[1
]}

Hughes, DL ^{[1
]}

机构：

[1] Merck & Co Inc, Merck Res Labs, Proc Res, Rahway, NJ 07065 USA

来源：

TETRAHEDRON | 2005年 / 61卷 / 26期

关键词：

D O I：

10.1016/j.tet.2005.03.143

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of a potent PDE IV inhibitor 1 is described. The synthesis is highlighted by two practical and efficient catalytic reactions: a highly selective catalytic palladium rnediated carbonylation of the pyridine side chain and an efficient palladiumcatalyzed Suzuki-Miyaura coupling of a chi oropyridi ne-N-oxide. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：6330 / 6336

页数：7

共 19 条

[1] Improved carbonylation of heterocyclic chlorides and electronically challenging aryl bromides [J].

Albaneze-Walker, J ;

Bazaral, C ;

Leavey, T ;

Dormer, PG ;

Murry, JA .

ORGANIC LETTERS, 2004, 6 (13) :2097-2100

[2]

[Anonymous], [No title captured], Patent No. 385210

[3]

Beller M, 2001, SYNTHESIS-STUTTGART, P1098, DOI 10.1055/s-2001-14576

[4] The preparation of pyridinecarboxylates from chloropyridines by the palladium-catalyzed alkoxycarbonylation [J].

Bessard, Y ;

Crettaz, R .

HETEROCYCLES, 1999, 51 (11) :2589-2602

[5] A practical, efficient, and rapid method for the oxidation of electron deficient pyridines using trifluoroacetic anhydride and hydrogen peroxide-urea complex [J].

Caron, S ;

Do, NM ;

Sieser, JE .

TETRAHEDRON LETTERS, 2000, 41 (14) :2299-2302

[6] Regiospecific carboalkoxylation of 2,5-dibromopyridine [J].

Chambers, RJ ;

Marfat, A .

SYNTHETIC COMMUNICATIONS, 1997, 27 (03) :515-520

[7] SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF NEW ARYLFLUORONAPHTHYRIDINE ANTIBACTERIAL AGENTS [J].

CHU, DTW ;

FERNANDES, PB ;

CLAIBORNE, AK ;

GRACEY, EH ;

PERNET, AG .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (11) :2363-2369

[8]

CHU DTW, 1990, J HETEROCYCLIC CHEM, V27, P1191

[9]

Dyke H J, 1999, Expert Opin Investig Drugs, V8, P1301, DOI 10.1517/13543784.8.9.1301

[10] PALLADIUM CATALYZED SYNTHESIS OF N-HETEROCYCLIC AND S-HETEROCYCLIC ESTERS [J].

HEAD, RA ;

IBBOTSON, A .

TETRAHEDRON LETTERS, 1984, 25 (51) :5939-5942

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