Organic Process Research and Development p. 775 - 782 (2019)
Update date:2022-08-17
Topics:
Remarchuk, Travis
Angelaud, Rémy
Askin, David
Kumar, Archana
Thompson, Andrew S.
Cheng, Hua
Reichwein, John F.
Chen, Yanping
St-Jean, Frédéric
Two convergent regioselective routes for the synthesis of the tetracyclic imidazobenzoxazepine triazole 1, a key intermediate toward the synthesis of taselisib, are described. In the first-generation route, a chemoselective Negishi cross-coupling reaction was developed between iodoimidazole 3 and triazole 7, which enabled the delivery of initial kilogram quantities of 1. Because of the inefficiencies in the preparation of the imidazole 3, a second-generation route via a highly regioselective imidazole ring formation between α-chloroketone 11 and aryl amidine 12 was developed. The resulting imidazole 14 provided the handle to efficiently install the seven-membered benzoxazepine ring system in one pot with two-step N-alkylation and SNAr tandem reactions.
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