Journal of Organic Chemistry p. 4921 - 4925 (2019)
Update date:2022-08-10
Topics:
Xie, Longfei
Am Ende, Christopher W.
Pettersson, Martin
Rankic, Danica A.
Sach, Neal W.
Sakya, Subbas
Humphrey, John M.
An efficient synthesis of pyridopyrazine-1,6-dione γ-secretase modulators (GSMs) is described. Our route features the construction of a crystalline lactone intermediate via a selective palladium-catalyzed 4-methylimidazole N1-arylation using the Buchwald Xantphos Pd G4 precatalyst, which does not require a preactivation step. The weak inorganic base KHCO3 was employed to minimize saponification of a particularly sensitive lactone substrate. Additional key transformations include DABAL-Me3-mediated lactone aminolysis and a mild TBD/ethyl trifluoroacetate mediated lactam ring closure to afford a representative GSM in high yield.
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Doi:10.1021/acs.orglett.9b00460
(2019)Doi:10.1016/j.jssc.2021.122018
(2021)Doi:10.1021/ja012714v
(2002)Doi:10.1016/0040-6031(95)02718-1
(1996)Doi:10.1021/ja01596a067
(1956)Doi:10.1002/smll.201500333
(2015)