Sodium Bicarbonate → HCID 23434084, compound

Participants

Reaction Steps

To a stirred solution of 1-chloro-3-(2-fluorophenyl)-5,6-dihydro-4H-cyclopenta(c)thiophene-4-one (118 mg, 0.443 mmol) in DME (7.5 mL) was added 4-pyridineboronic acid (130 mg, 1.06 mmol), saturated aqueous NaHCO3 solution (2.5 mL) and bis(triphenylphosphine)palladium(II)chloride (100 mg, 0.14 mmol) at room temperature under nitrogen. The mixture was heated at reflux temperature for 20 hours. The whole was extracted with ethyl acetate (50 mL×2), and the combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with hexane-ethyl acetate (1:1) to provide the title product (125 mg, 91% yield).

Provenance & Evidence