1,4-Dioxane → 2,2,2-trifluoroethyl 5-(2-(1-methyl-1H-pyrazol-3-yl)-4-(trifluoromethyl)phenyl)naphthalene-2-sulfonate

Participants

Reaction Conditions

Reaction Steps

A reaction vial was charged with 2,2,2-trifluoroethyl 5-bromonaphthalene-2-sulfonate (0.082 g, 0.222 mmol), (2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)boronic acid (0.072 g, 0.267 mmol), potassium phosphate tribasic (0.074 mL, 0.889 mmol) and Pd(PPh3)4 (0.026 g, 0.022 mmol). To this solid mixture was added dioxane (1.010 mL) followed by water (0.101 mL). The head space of the vial was swept with nitrogen and the vial was heated in an oil bath to 80° C. After stirring for 2 hours, LC/MS indicated that the reaction was complete. This reaction mixture was transferred to a separatory funnel containing water and the aqueous layer was washed three times with EtOAc. The organic layers were combined, dried with MgSO4, filtered and concentrated to an oil. The mixture was concentrated and purified by MPLC using 80 g of silica gel eluting with 0 to 40% EtOAc in hexanes to afford 0.11 g of 2,2,2-trifluoroethyl 5-(2-(1-methyl-1H-pyrazol-3-yl)-4-(trifluoromethyl)phenyl)naphthalene-2-sulfonate.

Provenance & Evidence