Synthesis of formylphenylpyridinecarboxylic acids using Suzuki-Miyaura coupling reactions

被引：0

作者：

Meier, P ^{[1
]}

Legraverant, S ^{[1
]}

Müller, S ^{[1
]}

Schaub, J ^{[1
]}

机构：

[1] Novartis Pharma AG, CCU, CT, Novartis Inst Biomed Res Basel, CH-4056 Basel, Switzerland

来源：

SYNTHESIS-STUTTGART | 2003年 / 04期

关键词：

cross-coupling; palladium catalyst; biaryls; heterocycles; pyridine carboxylic acids;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Formylphenylboronic acids were coupled with bromopyridylcarboxylic acids in the presence of a palladium catalyst. The yields of the different biaryls are strongly dependant on the substitution pattern of the two coupling partners. The electronic and steric effects of these are discussed.

引用

页码：551 / 554

页数：4

共 17 条

[1]

Boren J, 2001, J BIOL CHEM, V276, P37747

[2] STUDIES ON THE ACID HYDROLYSIS OF ALPHA-HALOGENATED PYRIDINE COMPOUNDS [J].

BRADLOW, HI ;

VANDERWERF, CA .

JOURNAL OF ORGANIC CHEMISTRY, 1949, 14 (04) :509-515

[3] Ligandless palladium catalyzed reactions of arylboronic acids and sodium tetraphenylborate with aryl halides in aqueous media [J].

Bumagin, NA ;

Bykov, VV .

TETRAHEDRON, 1997, 53 (42) :14437-14450

[4] Glivec (ST1571, Imatinib), a rationally developed, targeted anticancer drug [J].

Capdeville, R ;

Buchdunger, E ;

Zimmermann, J ;

Matter, A .

NATURE REVIEWS DRUG DISCOVERY, 2002, 1 (07) :493-502

[5] PHARMACOLOGICAL PROFILE OF VALSARTAN - A POTENT, ORALLY-ACTIVE, NONPEPTIDE ANTAGONIST OF THE ANGIOTENSIN-II AT1-RECEPTOR SUBTYPE [J].

CRISCIONE, L ;

DEGASPARO, M ;

BUHLMAYER, P ;

WHITEBREAD, S ;

RAMJOUE, HPR ;

WOOD, J .

BRITISH JOURNAL OF PHARMACOLOGY, 1993, 110 (02) :761-771

[6]

Farina V., 1997, ORG REACT, V50, P1, DOI DOI 10.1002/0471264180.or050.01

[7] Synthesis and SAR of benzamidine factor Xa inhibitors containing a vicinally-substituted heterocyclic core [J].

Fevig, JM ;

Pinto, DJ ;

Han, Q ;

Quan, ML ;

Pruitt, JR ;

Jacobson, IC ;

Galemmo, RA ;

Wang, SA ;

Orwat, MJ ;

Bostrom, LL ;

Knabb, RM ;

Wong, PC ;

Lam, PYS ;

Wexler, RR .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (05) :641-645

[8] Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].

Hassan, J ;

Sévignon, M ;

Gozzi, C ;

Schulz, E ;

Lemaire, M .

CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469

[9]

Heck R.F., 1985, PALLADIUM REAGENTS O

[10] Valsartan - A review of its pharmacology and therapeutic use in essential hypertension [J].

Markham, A ;

Goa, KL .

DRUGS, 1997, 54 (02) :299-311

← 1 2 →