Triethylamine → HCID 25030121, compound

Participants

Reaction Steps

A vial under nitrogen was charged with 2-(4,4-dimethyl-2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl trifluoromethanesulfonate (100 mg, 0.28 mmol), [4-(trifluoromethyl)phenyl]-boronic acid (58 mg, 0.31 mmol), and tetrakis(triphenylphosphine)palladium (65 mg, 0.056 mmol) followed by tetrahydrofuran (0.6 mL) and triethylamine (0.13 mL, 0.92 mmol). The mixture was stirred for 16 h, diluted with tetrahydrofuran, passed through a plug of silica gel (2 g) and concentrated. The crude product was purified by reverse phase HPLC to give the title compound. HRMS: calcd for C15H13F3N2O2S+H+, 343.07226; found (ESI-FT/MS, [M+H]1+), 343.0725; Analytical HPLC: purity 100% at 210-370 nm, 10.7 min; 100% at 268 nm, 10.7 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min

Provenance & Evidence