Scandium Triflate-Catalyzed N-[18F]Fluoroalkylation of Aryl- Or Heteroaryl-Amines with [18F]Epifluorohydrin under Mild Conditions

被引：3
|
作者：
Fujinaga, Masayuki [1 ]
Ohkubo, Takayuki [1 ]
Yamasaki, Tomoteru [1 ]
Kumata, Katsushi [1 ]
Nengaki, Nobuki [1 ]
Zhang, Ming-Rong [1 ]
机构：
[1] Natl Inst Quantum Sci & Technol, Inst Quantum Med Sci, Dept Adv Nucl Med Sci, Chiba, Chiba 2638555, Japan
来源：
ORGANIC LETTERS | 2022年 / 24卷 / 22期
关键词：
EFFICIENT METHOD; AUTOMATED SYNTHESIS; AROMATIC-AMINES; EPOXIDES; ALCOHOLS; RADIOSYNTHESIS; REACTIVITY; CLEAVAGE; CHLORIDE; LIGANDS;
D O I：
10.1021/acs.orglett.2c01459
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The scandium triflate-catalyzed N-[F-18]fluoroalkylation of aryl- or heteroaryl-amines with [F-18]epifluorohydrin ([F-18]2) was investigated. This reaction is mild and provides one-step access to N-[F-18]fluor oalkylated aryl- or heteroaryl-amines, which are used for positron emission tomography imaging. The use of 2,2,2-trifluoroethanol as a cosolvent improved the reaction efficiency. The use of (S)- and (R)-[F-18]2 produced the corresponding enantiomeric N-[F-18]fluoroalkylated anilines.
引用
收藏
页码：4024 / 4028
页数：5
相关论文
共 50 条
  • [41] The preliminary assessment of renal function of a 18F labeled hippurate analogue, N-(6-[18F]Fluoropyridin-3-yl)glycine, using two rat models
    Liu, Yang
    Dong, Weixuan
    Zhao, Qinan
    Xi, Rui
    Wu, Zhifang
    Lu, Keyi
    Wang, Hongliang
    Li, Sijin
    JOURNAL OF NUCLEAR MEDICINE, 2021, 62
  • [42] Selective targeting of melanoma using N-(2-diethylaminoethyl) 4-[18F]fluoroethoxy benzamide (4-[18F]FEBZA): a novel PET imaging probe
    Garg, Pradeep K.
    Nazih, Rachid
    Wu, Yanjun
    Grinevich, Vladimir P.
    Garg, Sudha
    EJNMMI RESEARCH, 2017, 7
  • [43] Automated synthesis of N-(2-[18F]Fluoropropionyl)-l-glutamic acid as an amino acid tracer for tumor imaging on a modified [18F]FDG synthesis module
    Liu, Shaoyu
    Sun, Aixia
    Zhang, Zhanwen
    Tang, Xiaolan
    Nie, Dahong
    Ma, Hui
    Jiang, Shende
    Tang, Ganghua
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2017, 60 (07): : 331 - 336
  • [44] Design and Synthesis of an Easily Obtainable Maleimide Reagent N-[2-(4-[18F]fluoro-N-methylbenzenesulfonamido)ethyl]maleimide ([18F]FBSEM) to Radiolabel Thiols in Proteins
    Fujita, Yuji
    Murakami, Yoshihiro
    Noda, Akihiro
    Miyoshi, Sosuke
    BIOCONJUGATE CHEMISTRY, 2017, 28 (02) : 642 - 648
  • [45] Substitution-reduction:: an alternative process for the [18F]N-(2-fluoroethylation) of anilines
    Briard, E
    Pike, VW
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2004, 47 (04): : 217 - 232
  • [46] (N-[18F]氟甲基)胆碱的合成与质量控制
    王劲
    程亮
    唐明灯
    庄达君
    国际放射医学核医学杂志, 2014, (03)
  • [47] Synthesis and evaluation of an N-[18F]fluorodeoxyglycosyl amino acid for PET imaging of tumor metabolism
    Wu, Zhifang
    Ma, Jingxin
    Brownell, Anna-Liisa
    Wang, Hongliang
    Li, Chaomin
    Meng, Xiaxia
    Yuan, Ling
    Liu, Haiyan
    Li, Sijin
    Xie, Jun
    NUCLEAR MEDICINE AND BIOLOGY, 2018, 66 : 40 - 48
  • [48] Synthesis of [18F]N-(2-fluoroethyl)clotrimazolium as a potential PET imaging agent
    Jung, S.
    Kim, I.
    Park, J.
    Kim, S.
    Hur, M.
    Choi, S.
    Yang, S.
    Yu, K.
    EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING, 2010, 37 : S360 - S360
  • [49] Radiation induced oxidation of [18F]fluorothia fatty acids under cGMP manufacturing conditions
    Pandey, Mukesh K.
    Jacobson, Mark S.
    Groth, Emily K.
    Tran, Natalie G.
    Lowe, Val J.
    DeGrado, Timothy R.
    NUCLEAR MEDICINE AND BIOLOGY, 2020, 80-81 : 13 - 23
  • [50] Xenon difluoride exchanges fluoride under mild conditions:: A simple preparation of [18F]xenon difluoride for PET and mechanistic studies
    Constantinou, M
    Aigbirhio, FI
    Smith, RG
    Ramsden, CA
    Pike, VW
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (08) : 1780 - 1781
12345