Sodium Carbonate → 3-(1-(2-Chlorophenyl)-1H-benzo[d][1,2,3]triazol-5-yl)-N-cyclopropyl-5-fluoro-4-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of N-cyclopropyl-3-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (100 mg, 0.31 mmol), 5-bromo-1-(2-chlorophenyl)-1H-benzo[d][1,2,3]triazole (110 mg, 0.34 mmol), tetrakis(triphenylphosphine)palladium(0) (18 mg, 0.016 mmol) in dioxane (3 mL) was added 1.3 mL of 2 N sodium carbonate solution. The reaction mixture was heated at 125° C. in a microwave for 30 min. The mixture was then treated with 2 mL of 1 N NaOH and extracted with 2×15 mL of EtOAc. The combined organic phase was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The resulting crude material was purified by flash chromatography on silical gel (30-70% of EtOAc in Hexanes) to give the title compound as an off white crystalline solid. MS (ESI, pos. ion) m/z: 421.0 (M+1).

Provenance & Evidence