1138239-36-7Relevant academic research and scientific papers
One-Pot Palladium-Catalyzed Cross-Coupling Treble of Borylation, the Suzuki Reaction and Amination
Jong, Howard,Eey, Stanley T.-C.,Lim, Yee Hwee,Pandey, Sangeeta,Iqbal, Nurul Azmah Bte,Yong, Fui Fong,Robins, Edward G.,Johannes, Charles W.
, p. 616 - 622 (2017)
A methodology for a sequential palladium-catalyzed cross-coupling procedure consisting of borylation, the Suzuki reaction and amination has been developed for the assembly of molecules with multi-aryl backbones. The linchpin of this development is the meta-terarylphosphine ligand, Cy*Phine, which has been employed as an air- and moisture-stable precatalyst, Pd(Cy*Phine)2Cl2, to improve the efficiency of one-pot borylation–Suzuki reactions. Additionally, the reactivity of the Pd-Cy*Phine system could be tuned to furnish a one-pot, borylation–Suzuki reaction–amination (BSA) cross-coupling treble. The methodology successfully integrated complementary conditions for three distinctly different and modular reactions. Average yields of 74–94% could be achieved for each segment that cumulatively afforded 50–84% yield over the entire three-step sequence in a single pot. (Figure presented.).
Stepwise Evolution of Fragment Hits against MAPK Interacting Kinases 1 and 2
Kwiatkowski, Jacek,Liu, Boping,Pang, Shermaine,Ahmad, Nur Huda Binte,Wang, Gang,Poulsen, Anders,Yang, Haiyan,Poh, Yong Rui,Tee, Doris Hui Ying,Ong, Esther,Retna, Priya,Dinie, Nurul,Kwek, Perlyn,Wee, John Liang Kuan,Manoharan, Vithya,Low, Choon Bing,Seah, Peck Gee,Pendharkar, Vishal,Sangthongpitag, Kanda,Joy, Joma,Baburajendran, Nithya,Jansson, Anna Elisabet,Nacro, Kassoum,Hill, Jeffrey,Keller, Thomas H.,Hung, Alvin W.
, p. 621 - 637 (2020)
Dysregulation of translation initiation factor 4E (eIF4E) activity occurs in various cancers. Mitogen-activated protein kinase (MAPK) interacting kinases 1 and 2 (MNK1 and MNK2) play a fundamental role in activation of eIF4E. Structure-activity relationship-driven expansion of a fragment hit led to discovery of dual MNK1 and MNK2 inhibitors based on a novel pyridine-benzamide scaffold. The compounds possess promising in vitro and in vivo pharmacokinetic profiles and show potent on target inhibition of eIF4E phosphorylation in cells.
Negishi cross-couplings compatible with unprotected amide functions
Manolikakes, Georg,Dong, Zhibing,Mayr, Herbert,Li, Jinshan,Knochel, Paul
supporting information; experimental part, p. 1324 - 1328 (2009/09/04)
The reaction conditions that allow a general Pd-catalyzed Negishi cross-coupling of a functionalized alkyl, aryl, heteroaryl, and benzylic zinc reagents with aryl acidic hydrogens were investigated. A dry and argon flushed 10 mL Schlenk-tube was charged with N-benzyl-4-bromobenzamide, Pd(OAc) 2, S-PHOS, and THF. 3-pentanoyl-benzylzinc chloride was added slowly over 90 minutes with a syringe pump. The reaction mixture was stirred for 1 hour at 25 °C. The reaction mixture was quenched with a saturated NH 4Cl solution and extracted with diethyl ether. The combined phases were then washed with a aqueous thiourea solution and dried over Na 2SO4. It was observed that the mild conditions considerably increase the ability of the Negishi cross-coupling in the synthesis of complex molecules and natural products.
