75833-63-5Relevant articles and documents
Atom Efficient Magnesiation of N-Substituted Alkyl Indoles with a Mixed Sodium-Magnesium Base
Stevens, Michael A.,Blair, Victoria L.
, p. 74 - 79 (2018/01/17)
This study presents the alkali metal mediated magnesiation (AMMMg) of three N-alkylated indoles with the mixed Na/Mg base [(TMEDA)Na(TMP)2Mg(CH2SiMe3)] 1 (TMEDA = N,N,N′,N′-tetramethylethylenediamine, TMP = 2,2,6,6-tetramethylpiperidine). All three magnesiated indoles have been successfully characterised by single-crystal X-ray diffraction and solution state NMR studies, whereas iodolysis and Pd-catalysed cross coupling have been investigated. The steric nature of the N-alkyl group changes the reactivity and efficiency of 1 to give either atom efficient disodium tetraindol-2-ylmagnesiates [(Na-TMEDA)2Mg(α-C9H8N)4] 2 and [(Na-TMEDA)2Mg(α-C10H11N)4] 3, or [(TMEDA)Na(TMP)(α-C11H12N)Mg(TMP)] 4, whereby only one indole molecule is selectively deprotonated.
ARYL RECEPTOR MODULATORS AND METHODS OF MAKING AND USING THE SAME
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Paragraph 00168-00169, (2016/04/26)
The present invention is generally directed towards compounds capable of binding the aryl hydrocarbon receptor and modulating its activity,methods of treating inflammatory conditions such as Crohn's disease using such compounds, and pharmaceutical compositions comprising such compounds. Also provided are methods of increasing levels of IL-22 in a subject and/or decreasing levels of IFN-γ in a subject.
σ-alkylpalladium intermediates in intramolecular Heck reactions: Isolation and catalytic activity
Beccalli, Egle M.,Borsini, Elena,Brenna, Stefano,Galli, Simona,Rigamonti, Micol,Broggini, Gianluigi
scheme or table, p. 1670 - 1678 (2010/06/15)
The isolation of σ-alkylpalladium Heck intermediates, possible when β-hydride elimination is inhibited, is a rather rare event. Performing intramolecular Heck reactions on Nallyl-2-halobenzylamines in the presence of [Pd(PPh3)4], we isolated and characterized a series of stable bridged palladacycles containing an iodine or bromine atom on the palladium atom. Indolyl substrates were also tested for isolation of the corresponding com- plexes. X-ray crystallographic analysis of one of the indolyl derivatives revealed the presence of a five-membered palladacycle with the metal center bearing a PPh3 ligand and an iodine atom in a cis position with respect to the nitrogen atom. The stability of the σ-alkylpalladium complexes is probably a consequence of the strong constraint resulting from the bridged junction that hampers the cisoid conformation essential for β-hydride elimination. Subsequently, the thus obtained bridged five-membered palladacycles were proven to be effective precatalysts in Heck reactions as well as in cross-coupling processes such as Suzuki and Stille reactions.