Water → N-(4-fluorophenyl)-1-(1,1,1-trifluoroprop-2-en-2-yl)phthalazin-6-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-chloro-N-(4-fluorophenyl)phthalazin-6-amine (0.300 g, 1.1 mmol), 4,4,6-trimethyl-2-(1,1,1-trifluoroprop-2-en-2-yl)-1,3,2-dioxaborinane (0.28 mL, 1.5 mmol), tetrakis(triphenylphosphine)palladium (0.063 g, 0.055 mmol) and sodium carbonate monohydrate (0.41 g, 3.3 mmol) in 6 mL of dioxane/water (3/1) was heated in a microwave at 100° C. for 40 min. Additional 4,4,6-trimethyl-2-(1,1,1-trifluoroprop-2-en-2-yl)-1,3,2-dioxaborinane (0.100 mL) and tetrakis(triphenylphosphine)palladium (0.063 g, 0.055 mmol) was added and the mixture was heated at 100° C. for an additional 30 min. After cooling to RT, water was added and the mixture was extracted with EtOAc (3×). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified on an ISCO column (12 g, 50-80% EtOAc in hexanes) to afford N-(4-fluorophenyl)-1-(1,1,1-trifluoroprop-2-en-2-yl)phthalazin-6-amine as a light yellow solid.

Provenance & Evidence