Sodium Carbonate Monohydrate → Methyl 4-methyl-3-(1-(1,1,1-trifluoroprop-2-en-2-yl)phthalazin-6-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 3-(1-chlorophthalazin-6-yl)-4-methylbenzoate (1.0 g, 3.2 mmol), 4,4,6-trimethyl-2-(1,1,1-trifluoroprop-2-en-2-yl)-1,3,2-dioxaborinane (0.99 g, 4.48 mmol), tetrakis(triphenylphosphine)palladium (185 mg, 0.16 mmol), and sodium carbonate monohydrate (1.2 g, 9.59 mmol) in dioxane/H2O (3:1, 12 mL) was heated in a microwave reactor at 100° C. for 80 min. The reaction mixture was partitioned between EtOAc (30 mL) and H2O (30 mL); the layers were separated, and the aqueous layer was extracted with EtOAc (2×30 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The resulting dark oil was dissolved in 2% Et3N in EtOAc, evaporated onto some silica gel, and purified by flash chromatography (Biotage Si 40+S, 20-60% of 2% Et3N in EtOAc/hexanes) to provide methyl 4-methyl-3-(1-(1,1,1-trifluoroprop-2-en-2-yl)phthalazin-6-yl)benzoate (833 mg, 70% yield) as a brown solid. MS (ESI, pos. ion) m/z: 373.2 (M+1).

Provenance & Evidence