Organic Process Research and Development p. 228 - 238 (2014)
Update date:2022-07-31
Topics:
Hong, Jun Bae
Davidson, James P.
Jin, Qingwu
Lee, Gary R.
Matchett, Michael
O'Brien, Erin
Welch, Michael
Bingenheimer, Bill
Sarma, Keshab
A scalable and convergent synthesis of a BTK (Bruton's tyrosine kinase) inhibitor has been developed. Synthetic routes to key intermediates were explored for the scale-up campaign, especially the process for 6-dimethylaminodihydroisoquinolinone, which was prepared via a regioselective cyclization of an isocyanate, mediated by AlCl3. Improved routes to key building blocks were demonstrated by expedient multikilogram productions. The target compound was assembled through a Pd-catalyzed amidation reaction followed by a Suzuki-Miyaura cross-coupling reaction.
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