Bromine → (S)-3-(3-(4-(5-amino-1,3,4-oxadiazol-2-yl)-3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(5-fluoropyridin-2-yl)oxazolidin-2-one

Participants

Reaction Steps

To a solution of (S,E)-2-(2-fluoro-4-(5-(4-(5-fluoropyridin-2-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzylidene)hydrazinecarboxamide (26 mg, 0.054 mmol) in acetic acid (0.6 mL) was added sodium acetate (44 mg, 0.54 mmol). After complete dissolution of the salt, a dilute solution of Br2 (2.7 μL, 0.054 mmol) in acetic acid was slowly added dropwise in portions. The reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was applied directly on a preparative TLC plate. Acetic acid was removed under a stream of air, and the preparative TLC plate was developed with 10% MeOH in DCM to afford (S)-3-(3-(4-(5-amino-1,3,4-oxadiazol-2-yl)-3-fluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(5-fluoropyridin-2-yl)oxazolidin-2-one (7.9 mg, 31% yield) as a yellow solid. MS (APCI+) m/z 477 [M+H]+.

Provenance & Evidence