Cesium fluoride → HCID 59781758, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-3-(trifluoromethyl)benzoic acid (APAC Pharmaceutical 680578, 15.0 g, 55.7 mmol), 2-fluorophenylboronic acid (9.4 g, 66.9 mmol), cesium fluoride (25.4 g, 167 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (5.7 g, 13.9 mmol) and palladium(II) acetate (1.25 g, 5.6 mmol) was prepared in dioxane (150 mL) and water (150 mL) under N2 atmosphere. The reaction mixture was purged with vacuum for 5 minutes, and then the reaction mixture was degassed with N2 at RT for 10 min. The reaction mixture was heated at 110° C. for 3 hours. The reaction mixture was cooled to RT and was filtered through a pad of Celite. The filtrate was concentrated under vacuum to afford a yellow solid. After purification by flash chromatography (silica, DCM containing 1% of AcOH), the title compound was obtained as a pale yellow powder. HPLC (Method A), Rt: 4.3 min (purity: 99.9%). UPLC/MS, M−(ESI): 283.0. 1H NMR (DMSO-d6, 300 MHz) δ 13.60 (s, 1H), 8.31 (d, J=1.4 Hz, 1H), 8.25 (dd, J=8.0, 1.4 Hz, 1H), 7.60 (d, J=8.0 Hz, 1H), 7.52 (m, 1H), 7.38-7.26 (m, 3H).

Provenance & Evidence