Potassium Fluoride → HCID 67341853, compound

Participants

Reaction Steps

3-{4-[2-(6-Chloro-pyridin-3-yl)-octyloxy]-benzoylamino}-propionic acid tert-butyl ester (180 mg, 0.369 mmol) is dissolved in toluene (2.5 mL), followed by palladium tetrakis triphenylphosphine (23 mg, 0.0197 mmol), 4-trifluoromethyl-phenyl boronic acid (81 mg, 0.43 mmol), and potassium fluoride (46 mg, 0.75 mmol). The reaction is purged with nitrogen and heated to reflux, then the water (2.5 mL) is added. The reaction is monitored by HPLC, and upon completion, allowed to cool to room temperature. The reaction is diluted with EtOAc and then celite added, followed by water. This mixture is then filtered through a pad of celite. The solution is separated in a separatory funnel, then the organic layer is washed with 0.1N sodium hydroxide, water, and brine. The organic layer is dried over anhydrous sodium sulfate, then concentrated. The product is purified by flash column chromatography (110 mg).

Provenance & Evidence