Development of an Efficient Manufacturing Process for Reversible Bruton’s Tyrosine Kinase Inhibitor GDC-0853 was written by 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. And the article was included in Organic Process Research & Development in 2018.Formula: C5H3Br2NO This article mentions the following:
Efforts toward the process development of reversible Bruton’s tyrosine kinase (BTK) inhibitor GDC-0853 are described. A practical synthesis of GDC-0853 was accomplished via a key highly regioselective Pd-catalyzed C-N coupling of tricyclic lactam with 2,4-dichloronicotinaldehyde to afford the C-N coupling product, a Suzuki-Miyaura cross-coupling of intermediate with boronic ester derived from a Pd-catalyzed borylation of tetracyclic bromide, to generate penultimate aldehyde intermediate and subsequent aldehyde reduction and recrystallization Process development of starting materials is also discussed. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-2-hydroxypyridine (cas: 13472-81-6Formula: C5H3Br2NO).
3,5-Dibromo-2-hydroxypyridine (cas: 13472-81-6) belongs to pyridine derivatives. In contrast to benzene, Pyridine’s electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Formula: C5H3Br2NO