Potassium Fluoride → HCID 59355967, compound

Participants

Reaction Steps

3-({5-[4,4,4-Trifluoro-1-(4-iodo-3,5-dimethyl-phenoxy)-butyl]-thiophene-2-carbonyl}-amino)-propionic acid methyl ester (300 mg, 0.53 mmol) was dissolved in toluene (1.5 mL), followed by palladium tetrakis triphenylphosphine (30 mg, 0.03 mmol), 4-isopropyl-phenyl boronic acid (173 mg, 1.05 mmol), and potassium fluoride (61.2 mg, 1.05 mmol). The reaction was purged with nitrogen and heated to reflux, then water (1.5 mL) was added. The reaction was monitored by HPLC, and upon completion, allowed to cool to room temperature. The reaction was diluted with EtOAc and then Celite® added, followed by water. This mixture was then filtered through a pad of Celite®. The solution was separated in a separatory funnel and the organic layer was washed with 0.1N sodium hydroxide, water, and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated. The product was purified by flash column chromatography (225 mg). MS(ES): 562.3 [M+H]+.

Provenance & Evidence