Novel Synthesis of 5-Amino-3-bromo-1-(tert-butyl)-1H-pyrazole-4-carbonitrile: A Versatile Intermediate for the Preparation of 5-Amino-3-aryl-1-(tert-butyl)-1H-pyrazole-4-carboxamides

被引：11
|
作者：
Bobko, Mark A. [1 ]
Kaura, Arun C. [1 ]
Evans, Karen A. [1 ]
Su, Dai-Shi [1 ]
机构：
[1] GlaxoSmithKline, Canc Res, Prot Dynam Discovery Performance Unit, Collegeville, PA 19426 USA
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 15期
关键词：
PYRAZOLES;
D O I：
10.1021/ol301655f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple, novel, and efficient route for the synthesis of 5-amino-3-aryl-1-(tert-butyl)-1H-pyrazole-4-carboxamides 1 has been devised. Preparation of pyrazole bromide 3 from potassium tricyanomethanide can be accomplished in only two steps in good yield and features a selective Sandmeyer reaction on the corresponding diaminopyrazole. This allows for a more versatile synthesis of 5-amino-3-aryl-1-(tert-butyl)-1H-pyrazole-4-carboxamides 1 than was previously possible.
引用
收藏
页码：3906 / 3908
页数：3
相关论文
共 50 条
  • [1] Reaction of 5-Amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile with Hydroxycyclohexanones
    Semenova, A. M.
    Oganesyan, R. V.
    Dotsenko, V. V.
    Chigorina, E. A.
    Aksenov, N. A.
    Aksenova, I. V.
    Netrebae, E. E.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2019, 89 (01) : 19 - 24
  • [2] Reaction of 5-Amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile with Hydroxycyclohexanones
    A. M. Semenova
    R. V. Oganesyan
    V. V. Dotsenko
    E. A. Chigorina
    N. A. Aksenov
    I. V. Aksenova
    E. E. Netrebae
    Russian Journal of General Chemistry, 2019, 89 : 19 - 24
  • [3] Ethyl 1-[5-amino-1-tert-butyl-3-(methylsulfanyl)-1H-pyrazole-4-carbonyl]-5-methyl-3-(methylsulfanyl)-1H-pyrazole-4-carboxylate
    Li, JF
    Song, HB
    Zhu, YQ
    Yang, HZ
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O1679 - O1681
  • [4] SYNTHESIS OF 1-AMINO-5-TERT-BUTYL-1H-PYRIMIDINE AND 3-AMINO-5-TERT-BUTYL-1H-PYRIMIDINE AND 3-AMINO-5-TERT-BUTYL-3H-V-TRIAZOLO[4,5-D]PYRIMIDINE AS HETARYNE PRECURSORS
    TIELEMANS, M
    CHRISTOPHE, D
    PROMEL, R
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (03) : 705 - 708
  • [5] 5-Amino-1-(2-chlorophenyl)-1H-pyrazole-4-carbonitrile
    Lin, Q-Lian
    Zhong, Ping
    Hu, Mao-Lin
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O3813 - U3061
  • [6] 5-Amino-3-anilino-1H-pyrazole-4-carbonitrile
    Mohamed, Shaaban K.
    Akkurt, Mehmet
    Fronczek, Frank R.
    EI-Remaily, Mahmoud A. A.
    Abdelhamid, Antar A.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O2784 - +
  • [7] Ethyl 1-tert-butyl-5-phenyl-1H-pyrazole-4-carboxylate
    Fun, Hoong-Kun
    Quah, Ching Kheng
    Chandrakantha, B.
    Isloor, Arun M.
    Shetty, Prakash
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O2228 - U1593
  • [8] Hydrogen-bonded chains in 3-tert-butyl-5-[(4-methoxybenzyl)amino]-1-phenyl-1H-pyrazole and tetramolecular hydrogen-bonded aggregates in 5-[(benzotriazol-1-ylmethyl)(4-methoxybenzyl)amino]-3-tert-butyl-1-phenyl-1H-pyrazole
    Abonia, Rodrigo
    Rengifo, Emerson
    Cobo, Justo
    Low, John N.
    Glidewell, Christopher
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2007, 63 : O29 - O32
  • [9] t-Butyl as a Pyrazole Protecting Group: Preparation and Use of 1-tert-Butyl-3-Methyl-1H-Pyrazole-5-Amine
    Pollock, Patrick M.
    Cole, Kevin P.
    Roberts, Scott W.
    Faul, Margaret
    ORGANIC SYNTHESES, 2012, 89 : 537 - 548
  • [10] 5-tert-Butyl-3-methyl-1H-pyrazole at 240 K
    Foces-Foces, CN
    Trofimenko, S
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2001, 57 : O32 - O34
12345