Potassium Carbonate → HCID 59192625, compound

Participants

Reaction Steps

To a degassed, stirred mixture of [5-(4-bromo-benzenesulfonylamino)-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-acetic acid tert-butyl ester (150 mg, 0.30 mmol) in 1,4-dioxane (10 mL) and a 1 M aqueous solution of potassium carbonate (0.89 mL, 0.89 mmol) was added 4-fluoro-pyridine-2-boronic acid (51 mg, 0.36 mmol) and tetrakis(triphenylphosphine)palladium(0) (16 mg, 0.014 mmol) under argon at room temperature. The mixture was heated at reflux for 4 hours. After being cooled to room temperature, the solvents were removed under reduced pressure. The crude residue was diluted with ethyl acetate (50 mL), washed with water (10 mL×2), dried over anhydrous sodium sulfate, and concentrated in vacuo to give crude {5-[4-(4-fluoro-pyridin-2-yl)-benzenesulfonylamino]-5,6,7,8-tetrahydro-naphthalen-1-yloxy}-acetic acid tert-butyl ester, which was used without further purification. MS cald. for C27H29FN2O5S 512, obsd. 513 [(M+H)+].

Provenance & Evidence