Potassium Carbonate → HCID 58238620, compound

Participants

Reaction Steps

Potassium carbonate (2.1 g, 15.0 mmol, 3.0 equiv) was dissolved in water (20 mL) and added to compound 5 (2.6 g, 5.0 mmol, 1.0 equiv) and phenylboronic acid (0.73 g, 6.0 mmol, 1.2 equiv) in dioxane (20 mL). A stream of nitrogen was bubbled through the solution for 15 min and tetrakis(triphenylphosphine)palladium(0) (0.03 g, 0.025 mmol, 0.005 equiv) was added to the reaction. The reaction was refluxed for 4 hr at which point LC/MS and TLC indicated the reaction to be complete. The reaction was allowed to cool to room temperature, diluted with ethyl acetate (50 mL), the organic layer was separated and washed with saturated brine (50 mL). The organic layer was dried over sodium sulfate and absorbed onto silica gel (7 g) by concentration under reduced pressure. This material was purified on a silica gel column (60 g) by eluting with heptanes (500 mL), ethyl acetate (1%) in heptanes (500 mL), ethyl acetate (2%) in heptanes (500 mL) and ethyl acetate (3%) in heptanes (500 mL). The desired product was isolated pure in 85% yield (2.2 g).

Provenance & Evidence