Potassium Carbonate → HCID 58238625, compound

Participants

Reaction Steps

Potassium carbonate (1.44 g, 10.5 mmol, 3.0 equiv) was dissolved in water (15 mL) and added to compound 9 (1.6 g, 3.5 mmol, 1.0 equiv) and phenylboronic acid (0.57 g, 4.2 mmol, 1.2 equiv) in dioxane (30 mL). A stream of nitrogen was bubbled through the solution for 15 min and tetrakis(triphenylphosphine)palladium(0) (0.02 g, 0.02 mmol, 0.005 equiv) was added to the reaction. The reaction was refluxed for 2 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 (5 g) by concentration under reduced pressure. This material was purified on a silica gel column (30 g) by eluting with ethyl acetate (1%) in heptanes (200 mL), ethyl acetate (2%) in heptanes (200 mL), ethyl acetate (3%) in heptanes (200 mL) and ethyl acetate (4%) in heptanes (200 mL). The desired product was isolated pure in 94% yield (1.5 g).

Provenance & Evidence