The first regioselective palladium-catalyzed indolization of 2-bromo- or 2-chloroanilines with internal alkynes: A new approach to 2,3-disubstituted indoles

被引:141
作者
Shen, M [1 ]
Li, GS [1 ]
Lu, BZ [1 ]
Hossain, A [1 ]
Roschangar, F [1 ]
Farina, V [1 ]
Senanayake, CH [1 ]
机构
[1] Boehringer Ingelheim Pharmaceut Inc, Dept Chem Dev, Richmond, VA 23219 USA
关键词
D O I
10.1021/ol048114t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first practical and economical process for synthesis of 2,3-disubstituted indole compounds has been developed with high regioselectivity by palladium-catalyzed indolization of 2-bromo- or chloroanilines and their derivatives with internal alkynes.
引用
收藏
页码:4129 / 4132
页数:4
相关论文
共 29 条
[1]   First palladium-catalyzed aminations of aryl chlorides [J].
Beller, M ;
Riermeier, TH ;
Reisinger, CP ;
Herrmann, WA .
TETRAHEDRON LETTERS, 1997, 38 (12) :2073-2074
[2]   SYNTHESIS OF THE 5-HT1D RECEPTOR AGONIST MK-0462 VIA A PD-CATALYZED COUPLING REACTION [J].
CHEN, CY ;
LIEBERMAN, DR ;
LARSEN, RD ;
REAMER, RA ;
VERHOEVEN, TR ;
REIDER, PJ ;
COTTRELL, IF ;
HOUGHTON, PG .
TETRAHEDRON LETTERS, 1994, 35 (38) :6981-6984
[3]   An efficient synthesis of the indole acetic acid metabolite of MK-0462 [J].
Chen, CY ;
Lieberman, DR ;
Street, LJ ;
Guiblin, AR ;
Larsen, RD ;
Verhoeven, TR .
SYNTHETIC COMMUNICATIONS, 1996, 26 (10) :1977-1984
[4]  
Faulkner DJ, 1999, NAT PROD REP, V16, P155
[5]   Room-temperature palladium-catalyzed amination of aryl bromides and chlorides and extended scope of aromatic C-N bond formation with a commercial ligand [J].
Hartwig, JF ;
Kawatsura, M ;
Hauck, SI ;
Shaughnessy, KH ;
Alcazar-Roman, LM .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5575-5580
[6]  
Hughes D. L., 1993, ORG PREP P INT, V25, P607
[7]   A NOVEL-APPROACH TO BZ-SUBSTITUTED TRYPTOPHANS VIA PD-CATALYZED COUPLING ANNULATION [J].
JESCHKE, T ;
WENSBO, D ;
ANNBY, U ;
GRONOWITZ, S ;
COHEN, LA .
TETRAHEDRON LETTERS, 1993, 34 (40) :6471-6474
[8]   Aqueous hydroxide as a base for palladium-catalyzed amination of aryl chlorides and bromides [J].
Kuwano, R ;
Utsunomiya, M ;
Hartwig, JF .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (18) :6479-6486
[9]   Synthesis of 2,3-disubstituted indoles via palladium-catalyzed annulation of internal alkynes [J].
Larock, RC ;
Yum, EK ;
Refvik, MD .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7652-7662
[10]   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