Sodium Iodide → HCID 70856732, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.8 g, 4.12 mmol) in acetonitrile (10 mL) was added cesium carbonate (3.36 g, 10.3 mmol, 2.5 eq), sodium iodide (0.124 g, 0.825 mmol, 0.2 eq) and (R)-ethyl 4-bromo-2-methyl-2-(methylsulfonyl)butanoate (1.54 g, 5.36 mmol, 1.3 eq). The mixture was heated at 50° C. overnight. The reaction mixture was filtered over a pad of diatomateous earth and the filtrate was evaporated to dryness. The crude product was purified by flash chromatography on silica gel eluting with 10-100% ethyl acetate/heptane to give ethyl (2R)-2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butanoate (0.810 g, 49% yield) as a white solid. LC-MS M+H+401.3.

Provenance & Evidence