A novel synthesis of N-(piperidin-4-yl)-1,3-dihydroindol-2-one via an intramolecular Pd-catalyzed amination

被引:20
作者
van den Hoogenband, A [1 ]
den Hartog, JAJ [1 ]
Lange, JHM [1 ]
Terpstra, JW [1 ]
机构
[1] Solvay Pharmaceut, Res Labs, NL-1381 CP Weesp, Netherlands
关键词
D O I
10.1016/j.tetlet.2004.09.121
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel efficient synthetic route to the pharmaceutical key intermediate N-(piperidin-4-yl)-1,3-dihydroindol-2-one is described. The key step involves a high-yielding intramolecular palladium-catalyzed amination reaction using Buchwald's X-Phos ligand under mild reaction conditions. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8535 / 8537
页数:3
相关论文
共 20 条
  • [1] ASMAWI MZ, 1988, EICOSANOIDS, V1, P35
  • [2] A short and efficient synthesis of N-substituted indol-2-ones (oxindoles)
    Forbes, IT
    [J]. TETRAHEDRON LETTERS, 2001, 42 (39) : 6943 - 6945
  • [3] Efficient palladium-catalyzed coupling of aryl chlorides and tosylates with terminal alkynes: Use of a copper cocatalyst inhibits the reaction
    Gelman, D
    Buchwald, SL
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (48) : 5993 - 5996
  • [4] Expanding Pd-catalyzed C-N bond-forming processes: The first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions
    Huang, XH
    Anderson, KW
    Zim, D
    Jiang, L
    Klapars, A
    Buchwald, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) : 6653 - 6655
  • [5] Wide bite angle diphosphines: Xantphos ligands in transition metal complexes and catalysis
    Kamer, PCJ
    van Leeuwen, PWN
    Reek, JNH
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (11) : 895 - 904
  • [6] Microwave-enhanced Goldberg reaction:: a novel route to N-arylpiperazinones and N-arylpiperazinediones
    Lange, JHM
    Hofmeyer, LJF
    Hout, FAS
    Osnabrug, SJM
    Verveer, PC
    Kruse, CG
    Feenstra, RW
    [J]. TETRAHEDRON LETTERS, 2002, 43 (06) : 1101 - 1104
  • [7] LOVELY CJ, 2004, TETRAHEDRON, V60, P359
  • [8] MACH R, 1998, J MED CHEM, V41, P2361
  • [9] Mokrosz MJ, 1998, ARCH PHARM, V331, P325, DOI 10.1002/(SICI)1521-4184(199810)331:10<325::AID-ARDP325>3.0.CO
  • [10] 2-6