Concise and efficient synthesis of 4-fluoro-1H-pyrrolo[2,3-b]pyridine

被引：42
|
作者：
Thibault, C [1 ]
L'Heureux, A [1 ]
Bhide, RS [1 ]
Ruel, R [1 ]
机构：
[1] Bristol Myers Squibb Co, Dept Discovery Chem, Pharmaceut Res Inst, Quebec City, PQ J5R 1J1, Canada
来源：
ORGANIC LETTERS | 2003年 / 5卷 / 26期
关键词：
D O I：
10.1021/ol036030z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] Two routes describing the preparation of 4-fluoro-1H-pyrrolo[2,3-b]pyridine (4a) from 1H-pyrrolo[2,3-b]pyridine N-oxide (1) are presented, Regioselective fluorination was achieved using either the Balz-Schiemann reaction or lithium-halogen exchange.
引用
收藏
页码：5023 / 5025
页数：3
相关论文
共 50 条
  • [21] Gold catalysis in the synthesis of azaindoles: pyrrolo[2,3-b]pyridines and pyrrolo[2,3-b]pyrazines
    Gala, Elena
    Cordoba, Marta
    Luisa Izquierdo, M.
    Alvarez-Builla, Julio
    ARKIVOC, 2014, : 319 - 340
  • [22] Synthesis of 1H-pyrrolo[2,3-b]phenoxathiin-2,3-dione
    Loloiu, G
    Loloiu, T
    Maior, O
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1998, (03): : 396 - 399
  • [23] Synthesis of 1H-pyrrolo[2,3-b]phenoxathiin-2,3-dione
    Chem. Heterocycl. Compd., 3 (363-366):
  • [24] Synthesis of 1H-pyrrolo[2,3-b]phenoxathiin-2,3-dione
    Loloiu G.
    Loloiu T.
    Maior O.
    Chemistry of Heterocyclic Compounds, 1998, 34 (3) : 363 - 366
  • [25] HECK ANNULATION ON 2-POSITION OF INDOLES OR 1H-PYRROLO[2,3-B]PYRIDINE
    DESARBRE, E
    MEROUR, JY
    HETEROCYCLES, 1995, 41 (09) : 1987 - 1998
  • [26] Synthesis and SAR Studies of 1H-Pyrrolo[2,3-b]pyridine-2-carboxamides as Phosphodiesterase 4B (PDE4B) Inhibitors
    Vadukoot, Anish K.
    Sharma, Swagat
    Aretz, Christopher D.
    Kumar, Sushil
    Gautam, Nagsen
    Alnouti, Yazen
    Aldrich, Amy L.
    Heim, Cortney E.
    Kielian, Tammy
    Hopkins, Corey R.
    ACS MEDICINAL CHEMISTRY LETTERS, 2020, 11 (10): : 1848 - 1854
  • [27] PYRROLOQUINOLINES .2. SYNTHESIS OF H-1-PYRROLO[2,3-B]QUINOLINES
    MURUGESAN, M
    SOUNDARARAJAN, N
    RAMASAMY, K
    SHANMUGAM, P
    SYNTHESIS-STUTTGART, 1979, (05): : 352 - 354
  • [28] Synthesis, Crystal Structure and DFT Study of 5-Bromo-1-Tosyl-1H-Pyrrolo[2,3-b]Pyridine
    T. Cheng
    J. Jing
    C. -Y. Yang
    D. -N. Nie
    K. -M. Yang
    S. Tang
    S. -X. Fu
    Y. -N. Zhang
    Z. -X. Zhou
    Journal of Structural Chemistry, 2023, 64 : 1369 - 1379
  • [29] Synthesis of the 7-azaindole (1H-pyrrolo[2,3-b]pyridine) analogous to cannabimimetic JHW 200
    Gluszok, Sebastien
    Goossens, Laurence
    Depreux, Patrick
    Barbry, Didier
    Henichart, Jean-Pierre
    SYNTHETIC COMMUNICATIONS, 2006, 36 (19) : 2797 - 2805
  • [30] SYNTHESIS, CRYSTAL STRUCTURE AND DFT STUDY OF 5-BROMO-1-TOSYL-1H-PYRROLO[2,3-B]PYRIDINE
    Cheng, T.
    Jing, J.
    Yang, C. -Y.
    Nie, D. -N.
    Yang, K. -M.
    Tang, S.
    Fu, S. -X.
    Zhang, Y. -N.
    Zhou, Z. -X.
    JOURNAL OF STRUCTURAL CHEMISTRY, 2023, 64 (08) : 1369 - 1379
12345