Preparation of 6-chloro-5-fluoroindole via the use of palladium and copper-mediated heterocyclisations

被引:20
作者
Adams, DR [1 ]
Duncton, MAJ [1 ]
Roffey, JRA [1 ]
Spencer, J [1 ]
机构
[1] Vernalis Res Ltd, Dept Chem, Woking RG41 5UA, Surrey, England
关键词
indoles; palladium and compounds; catalysis; coupling reactions;
D O I
10.1016/S0040-4039(02)01758-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title indole, the heterocyclic core of the 5-HT2C receptor agonist Ro 60-0175, was prepared by it modification to the Stille indole synthesis, or by the method of Gonzalez and co-workers. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7581 / 7583
页数:3
相关论文
共 9 条
[1]  
[Anonymous], TETRAHEDRON ORGANIC
[2]   Novel agonists of 5HT(2C) receptors. Synthesis and biological evaluation of substituted 2-(indol-1-yl)-1-methylethylamines and 2-(indeno[1,2-b]pyrrol-1-yl)-1-methylethylamines. Improved therapeutics for obsessive compulsive disorder [J].
Bos, M ;
Jenck, F ;
Martin, JR ;
Moreau, JL ;
Sleight, AJ ;
Wichmann, J ;
Widmer, U .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (17) :2762-2769
[3]   Palladium catalyzed cross-coupling reaction of Grignard reagents with halobenzoic acids, halophenols and haloanilines [J].
Bumagin, NA ;
Luzikova, EV .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 532 (1-2) :271-273
[4]   Efficient reagents for the synthesis of 5-, 7-, and 5,7-substituted indoles starting from aromatic amines: Scope and limitations [J].
Ezquerra, J ;
Pedregal, C ;
Lamas, C ;
Barluenga, J ;
Perez, M ;
GarciaMartin, MA ;
Gonzalez, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) :5804-5812
[5]  
HARMATA M, 1995, SYNTHESIS-STUTTGART, P713
[6]   TRANSITION-METALS IN THE SYNTHESIS AND FUNCTIONALIZATION OF INDOLES [J].
HEGEDUS, LS .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (09) :1113-1226
[7]  
ISHIKURA T, 1989, Patent No. 01311056
[8]   PALLADIUM-CATALYZED COUPLING OF 2-BROMOANILINES WITH VINYLSTANNANES - A REGIOCONTROLLED SYNTHESIS OF SUBSTITUTED INDOLES [J].
KROLSKI, ME ;
RENALDO, AF ;
RUDISILL, DE ;
STILLE, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (06) :1170-1176
[9]   SYNTHESIS OF INDOLES VIA PALLADIUM-CATALYZED HETEROANNULATION OF INTERNAL ALKYNES [J].
LAROCK, RC ;
YUM, EK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (17) :6689-6690