Palladium-Catalyzed Cross-Coupling between 7-Azaindoles and Reformatsky Reagents

被引:9
作者
Barl, Nadja M. [1 ]
Malakhov, Vladimir [1 ]
Mathes, Christian [2 ]
Lustenberger, Philipp [2 ]
Knochel, Paul [1 ]
机构
[1] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
[2] Novartis Pharma AG, CH-4056 Basel, Switzerland
来源
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 05期
基金
欧洲研究理事会;
关键词
azaindole; Reformatsky reagents; metalation; palladium; cross-coupling; FUNCTIONALIZED ORGANOZINC REAGENTS; INHIBITORY-ACTIVITY; CARBON-DIOXIDE; ZINCATION; REACTIVITY; AZAINDOLES; ALDEHYDES; HALIDES; KETONES; POTENT;
D O I
10.1055/s-0034-1379459
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The preparation of various 2-(7-azaindolyl)carboxylic esters by Pd-catalyzed coupling of Reformatsky reagents with TBDMS-protected 3-bromo-7-azaindoles leading to a wide range of arylated ester derivatives is reported. After removal of the protecting group, the corresponding free 2-(7-azaindolyl)carboxylic esters are obtained in satisfactory yields.
引用
收藏
页码:692 / 700
页数:9
相关论文
共 27 条
[1]  
Alvarez M, 1999, SYNTHESIS-STUTTGART, P615
[2]   Direct Addition of Functionalized Organozinc Reagents to Carbon Dioxide, Ketones, and Aldehydes in the Presence of MgCl2 [J].
Bernhardt, Sebastian ;
Metzger, Albrecht ;
Knochel, Paul .
SYNTHESIS-STUTTGART, 2010, (22) :3802-3810
[3]  
Blake J, 2009, Patent PCT Int. Appl., Patent No. [WO 2009089352, 2009089352]
[4]   Pd-Catalyzed α-Arylation of Nitriles and Esters and γ-Arylation of Unsaturated Nitriles with TMPZnCl•LiCl [J].
Duez, Stephanie ;
Bernhardt, Sebastian ;
Heppekausen, Johannes ;
Fleming, Fraser F. ;
Knocher, Paul .
ORGANIC LETTERS, 2011, 13 (07) :1690-1693
[5]   Meriolins (3-(pyrimidin-4-yl)-7-azaindoles): Synthesis, kinase inhibitory activity, cellular effects, and structure of a CDK2/cyclin A/meriolin complex [J].
Echalier, Aude ;
Bettayeb, Karima ;
Ferandin, Yoan ;
Lozach, Olivier ;
Clement, Monique ;
Valette, Annie ;
Liger, Franrcois ;
Marquet, Bernard ;
Morris, Jonathan C. ;
Endicott, Jane A. ;
Joseph, Benoit ;
Meijer, Laurent .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (04) :737-751
[6]   6-amino-2-(4-fluorophenyl)-4-methoxy-3(4-pyridyl)-1H-pyrrolo[2,3-b]pyridine (RWJ 68354):: A potent and selective p38 kinase inhibitor [J].
Henry, JR ;
Rupert, KC ;
Dodd, JH ;
Turchi, IJ ;
Wadsworth, SA ;
Cavender, DE ;
Fahmy, B ;
Olini, GC ;
Davis, JE ;
Pellegrino-Gensey, JL ;
Schafer, PH ;
Siekierka, JJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (22) :4196-4198
[7]  
Kaila N, 2011, US Pat. Appl. Publ US, Patent No. 20110105509
[8]   Lewis Acid-Triggered Selective Zincation of Chromones, Quinolones, and Thiochromones: Application to the Preparation of Natural Flavones and Isoflavones [J].
Klier, Lydia ;
Bresser, Tomke ;
Nigst, Tobias A. ;
Karaghiosoff, Konstantin ;
Knochel, Paul .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13584-13587
[9]  
Knochel P, 2011, Int. Appl, Patent No. [WO 2011113925, 2011113925]
[10]   Recent advances in the synthesis and properties of 4-, 5-, 6-or 7-azaindoles [J].
Merour, Jean-Yves ;
Routier, Sylvain ;
Suzenet, Franck ;
Joseph, Benoit .
TETRAHEDRON, 2013, 69 (24) :4767-4834