13472-81-6Relevant articles and documents
Magnesiate-Utilized/Benzyne-Mediated Approach to Indenopyridones from 2-Pyridones: An Attempt to Synthesize the Indenopyridine Core of Haouamine
Idzik, Tomasz J.,Borzyszkowska-Ledwig, Aleksandra,Struk, ?ukasz,So?nicki, Jacek G.
supporting information, p. 9667 - 9671 (2019/11/29)
An efficient, short-staged synthesis of cis-fused indeno[2,1-b]- and indeno[1,2-c]pyridin-2-ones, starting from 2-pyridones, using magnesiates of type R3MgLi as nucleophilic and deprotonation agents, mediated by benzyne generated in situ, under optimized conditions, is described. Following the developed protocol, rare C4a-arylsubstituted indeno[2,1-b]pyridones, resembling the core of haouamine, were obtained. The protocol offering the one-pot synthesis directly from 2-pyridone is also described.
Development of an Efficient Manufacturing Process for Reversible Bruton's Tyrosine Kinase Inhibitor GDC-0853
Zhang, Haiming,Cravillion, Theresa,Lim, Ngiap-Kie,Tian, Qingping,Beaudry, Danial,Defreese, Jessica L.,Fettes, Alec,James, Philippe,Linder, David,Malhotra, Sushant,Han, Chong,Angelaud, Remy,Gosselin, Francis
, p. 978 - 990 (2018/07/15)
Efforts toward the process development of reversible Bruton's tyrosine kinase (BTK) inhibitor GDC-0853 (1) are described. A practical synthesis of GDC-0853 was accomplished via a key highly regioselective Pd-catalyzed C-N coupling of tricyclic lactam 5 with 2,4-dichloronicotinaldehyde (6) to afford the C-N coupling product 3, a Suzuki-Miyaura cross-coupling of intermediate 3 with boronic ester 4 derived from a Pd-catalyzed borylation of tetracyclic bromide 7, to generate penultimate aldehyde intermediate 2 and subsequent aldehyde reduction and recrystallization. Process development of starting materials 5, 6, and 7 is also discussed.
Mild regioselective halogenation of activated pyridines with N-bromosuccinimide
Canibano,Rodriguez,Santos,Sanz-Tejedor,Carreno,Gonzalez,Garcia-Ruano
, p. 2175 - 2179 (2007/10/03)
Regioselective mono and dihalogenations of amino, hydroxy and methoxy pyridines (2-, 3-, and 4-substituted) as well as 2,6-dimethoxy pyridine with N-bromosuccinimide in different solvents have been studied. Reactivity of the substrates decreases in the order amino>hydroxy>methoxy and regioselectivity depends on the position of the substituent (2-substituted > 3-substituted). In most of the cases we obtained monobrominated derivatives regioselectively and in high yields. Hydroxy and amino pyridines can also be dibrominated in almost quantitative yield with 2 equivalents of NBS.
