Organic Process Research and Development p. 978 - 990 (2018)
Update date:2022-08-29
Topics:
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
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.
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Tianjin Crest Pharmaceutical R&D Co., Ltd. (Tianjin Yao Technology Development Co., Ltd.)
Contact:+86-22-66211386
Address:Building B5-405, No, 80 4th Avenue, TEDA, Tianjin, China P.R. 300457
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