594827-31-3Relevant academic research and scientific papers
Ir-Catalyzed Reversible Acceptorless Dehydrogenation/Hydrogenation of N-Substituted and Unsubstituted Heterocycles Enabled by a Polymer-Cross-Linking Bisphosphine
Zhang, Deliang,Iwai, Tomohiro,Sawamura, Masaya
supporting information, p. 5240 - 5245 (2020/07/03)
The polystyrene-cross-linking bisphosphine ligand PS-DPPBz was effective for the Ir-catalyzed reversible acceptorless dehydrogenation/hydrogenation of N-heterocycles. Notably, this protocol is applicable to the dehydrogenation of N-substituted indoline derivatives with various N-substituents with different electronic and steric natures. A reaction pathway involving oxidative addition of an N-adjacent C(sp3)-H bond to a bisphosphine-coordinated Ir(I) center is proposed for the dehydrogenation of N-substituted substrates.
Replacement of Stoichiometric DDQ with a Low Potential o-Quinone Catalyst Enabling Aerobic Dehydrogenation of Tertiary Indolines in Pharmaceutical Intermediates
Li, Bao,Wendlandt, Alison E.,Stahl, Shannon S.
supporting information, p. 1176 - 1181 (2019/02/14)
A transition-metal/quinone complex, [Ru(phd)3]2+ (phd = 1,10-phenanthroline-5,6-dione), is shown to be effective for aerobic dehydrogenation of 3° indolines to the corresponding indoles. The results show how low potential quinones may be tailored to provide a catalytic alternative to stoichiometric DDQ, due to their ability to mediate efficient substrate dehydrogenation while also being compatible with facile reoxidation by O2. The utility of the method is demonstrated in the synthesis of key intermediates to pharmaceutically important molecules.
[11C]Enzastaurin, the first design and radiosynthesis of a new potential PET agent for imaging of protein kinase C
Wang, Min,Xu, Lu,Gao, Mingzhang,Miller, Kathy D.,Sledge, George W.,Zheng, Qi-Huang
experimental part, p. 1649 - 1653 (2011/05/11)
Enzastaurin (LY317615) is a potent and selective protein kinase C (PKC) inhibitor with an IC50 value of ～6 nM. [11C] Enzastaurin (3-(1-[11C]methyl-1H-indol-3-yl)-4-[1-[1-(2- pyridinylmethyl)-4-piperidinyl]-1H-indol-3-yl]-1H-pyrrole-2,5-dione), a new potential PET agent for imaging of PKC, was first designed and synthesized in 20-25% decay corrected radiochemical yield and 370-555 GBq/μmol specific activity at end of bombardment (EOB). The synthetic strategy was to prepare a carbon-11-labeled maleic anhydride intermediate followed by the conversion to maleimide.
Development of a manufacturing process for 1-(1-pyridin-2-yl methyl-piperidin-4-yl)-1H-indole: A key intermediate for protein kinase C inhibitor LY317615
Boini, Sathish,Moder, Kenneth P.,Vaid, Radhe K.,Kopach, Micheal,Kobierski
, p. 1205 - 1211 (2012/12/23)
This contribution describes process development leading to the production of 1-(1-pyridin-2-yl methyl-piperidin-4-yl)-1H-indole (11). The title compound 11 was produced via a Leimgruber-Batcho indole synthesis using key intermediates 2-(2,2-dimethoxyethyl
Strategies for the synthesis of N-(azacycloalkyl)bisindolylmaleimides: Selective inhibitors of PKCβ
Faul, Margaret M.,Grutsch, John L.,Kobierski, Michael E.,Kopach, Michael E.,Krumrich, Christine A.,Staszak, Michael A.,Udodong, Uko,Vicenzi, Jeffrey T.,Sullivan, Kevin A.
, p. 7215 - 7229 (2007/10/03)
N-(Azacycloalkyl)bisindolylmaleimides 1 have been identified to be selective inhibitors of PKCβ. This manuscript will describe the synthetic approaches employed to prepare this class of compounds that resulted in development of efficient methods for prepa
