Potassium Phosphate, Tribasic → 4-(2-Fluoropyridin-3-YL)cyclohex-3-enol

Participants

Reaction Steps

To a 25 mL microwave vial was added potassium phosphate tribasic (0.354 mL, 4.27 mmol), PdCl2(AmPhos) (0.121 g, 0.171 mmol), 4-(tert-butyldimethylsilyloxy)cyclohex-1-enyl trifluoromethanesulfonate (0.616 g, 1.710 mmol), and 2-fluoropyridin-3-ylboronic acid (0.265 g, 1.881 mmol) before evacuating and backfilling with nitrogen (3×). A mixed solvent of Dioxane (7.12 mL):water (1.425 mL) was added, and the contents were irradiated at 150° C. for 30 minutes in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden). The biphasic solution was diluted with water and extracted with DCM (3×25 mL) before drying over sodium sulfate, filtering, and concentrating under reduced pressure to a dark brown residue. The residue was taken up in 5 mL DCM and applied directly to silica (0 to 70% ethyl acetate/hexanes for followed by 5 to 10% MeOH/DCM). The resulting yellow oil was taken forward without further manipulation.

Provenance & Evidence