Potassium Carbonate → (5R)-3-(3-Fluoro-4-{6-[(5R)-5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]pyridin-3-yl}phenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

[(5R)-3-(5-Bromopyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methanol (intermediate 12, 0.139 g, 0.54 mmol), (5R)-3-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (Intermediate 7, 0.2 g, 0.514 mmol), potassium carbonate (0.355 g, 2.57 mmol), and tetrakis(triphenylphosphino)palladium(0) (0.059 g, 0.05 mmol) were combined and suspended in DMF (7 ml) and water (1 ml). The mixture was heated at 75° C. for 2 hours, then was poured into cold water (30 ml). The solids formed were collected, rinsed with water and washed with dichloromethane (2×10 ml), the solids were further purified by column chromatography, eluted with 5% DMF in dichloromethane to give the title compound as a white solid (0.125 g).

Provenance & Evidence