Synthesis of 5-chloro-7-azaindoles by Fischer reaction

31st Annual GP2A Medicinal Chemistry Conference

“…Heck-type palladocatalyzed cyclization reactions are presented, using various fluoro-iodo-aminopyridines and optimizations of their synthesis through stereoselective electrophilic iodinations. This robust strategy of pyridine iodination/cyclization step will give versatile access to the desired azaindole scaffolds [97,98] The development of fluorescent probes for intracellular allosteric sites represents a significant advance in the field of medicinal chemistry. In this study, we present the design, synthesis, and evaluation of the first fluorescent probe targeting the intracellular allosteric site of the neurotensin receptor 1 (NTSR1).…”

“…This receptor plays a critical role in various physiological processes and is a promising therapeutic target for a range of Heck-type palladocatalyzed cyclization reactions are presented, using various fluoroiodo-aminopyridines and optimizations of their synthesis through stereoselective electrophilic iodinations. This robust strategy of pyridine iodination/cyclization step will give versatile access to the desired azaindole scaffolds [97,98] Department of Chemistry and Pharmacy, Friedrich-Alexander University Erlangen, 91058 Erlangen, Germany; patrick.shinkwin@fau.de 2.…”

Design, Synthesis, Molecular Docking Study and Biological Evaluation of Novel γ-Carboline Derivatives of Latrepirdine (Dimebon) as Potent Anticancer Agents

“…To obtain compound 9, the synthesis of imine 6 as an intermediate was synthesized using a condensation reaction between 2-bromo-6-hydrazinylpyridine (4) and 1-methylpiperidin-4-one (5). Imine 6, reacted with hot PPA at 180 • C for 24 h which produced γ-Carboline 7 [18,19]. N-alkylation of compound 7 was achieved using a cesium carbonate base.…”

“…3, 51.4, 45.7, 43.5, 36.6, 22.8. 19 F NMR (500 MHz, CDCl 3 ) δ: −115.2. .09 (dd, 2H, J = 7.8, 1.5 Hz), 4.45 (t, 2H J = 7.5 Hz), 3.64 (s, 2H), 3.14 (t, 2H, J = 7.5 Hz), 2.73 (t, 2H, J = 5.5 Hz), 2.60 (t, 2H, J = 5.5 Hz), 2.53 (s, 3H).…”