Ethyl 4-iodobenzoate → HCID 67553060, compound

Participants

Reaction Steps

A solution of 6-ethynyl-7-fluoro-2,2-dimethylthiochroman-4-one (Compound 207, 330.0 mg, 1.41 mmol) and ethyl 4-iodobenzoate (392 mg, 1.41 mmol) in 10.0 mL Et3N was purged with argon for 15 minutes. To this solution was added bis(triphenylphosphine)-palladium(II) chloride (247 mg, 0.35 mmol) and copper(I) iodide (67.0 mg, 0.35 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 (3 to 5% EtOAc/hexanes) of the residual solid afforded 490.0 mg (91%) of the title compound as a yellow solid. 1H NMR (300 MHz, CDCl3)δ: 8.31 (1H, d, J=7.6 Hz), 8.04 (2H, d, J=8.3 Hz), 7.60 (2H, d, J=8.3 Hz), 7.00 (1H, d, J=9.3 Hz), 4.40 (2H, q, J=7.1 Hz), 2.89 (2H, s), 1.50 (6H, s), 1.41 (3H, t, J=7.1 Hz).

Provenance & Evidence