Ethyl 4-iodobenzoate → HCID 21846648, compound

Participants

Reaction Steps

A solution of 6-ethynyl-7-methoxy-2,2-dimethylthiochroman-4-one (Compound 208, 217.0 mg, 0.88 mmol) and ethyl 4-iodobenzoate (245.0 mg, 0.89 mmol) in 10.0 mL Et3N and 2 mL THF was purged with argon for 15 minutes. To this solution was added bis(triphenylphosphine)-palladium(II) chloride (154.0 mg, 0.22 mmol) and copper(I) iodide (42.0 mg, 0.22 mmol). After sparging for an additional 10 minutes with argon, the solution was stirred overnight at room temperature. The reaction mixture was diluted with EtOAc and filtered through a pad of Celite using an EtOAc wash. Concentration of the filtrate under reduced pressure, followed by column chromatography (5 to 10% EtOAc/hexanes) of the residual solid afforded 320.0 mg (92%) of the title compound as an orange solid. 1H NMR (300 MHz, CDCQ3)δ: 8.29 (1H, s), 8.03 (2H, d, J=8.4 Hz), 7.60 (2H, d, J=8.4 Hz), 6.70 (1H, s), 4.40 (2H, q, J=7.1 Hz), 3.96 (3H, s), 2.86 (2H, s), 1.50 (6H, s), 1.41 (3H, t, J=7.1 Hz).

Provenance & Evidence