Sodium Carbonate → (S)-3-(3-(3-fluoro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(pyridin-2-yl)oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(pyridin-2-yl)oxazolidin-2-one (0.25 g, 0.69 mmol) in dioxanes (70 mL) purged continuously with nitrogen gas was added 3-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazole (0.44 g, 1.0 mmol) and sodium carbonate (1.7 mL, 3.5 mmol) (2M in water). Pd2 dba3 (70 mg) and X-Phos (70 mg) were added, and the reaction mixture was stirred at 80° C. for 3 hours, then diluted with EtOAc (200 mL). The organic layer was washed with water and brine, dried over MgSO4, filtered concentrated in vacuo. The crude material was chromatographed using 50% EtOAc/hexane as eluent to yield (S)-3-(3-(3-fluoro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(pyridin-2-yl)oxazolidin-2-one (0.090 g, 22.5%).

Provenance & Evidence