Sodium Carbonate → HCID 59054130, compound

Participants

Reaction Steps

To a mixture of 2-(3-bromo-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-sulfonic acid cyclobutylamide (748.1 mg, 1.67 mmol), 2-hydroxy-phenylboronic acid (276.0 mg, 2.0 mmol) and tetrakis(triphenylphosphine)palladium(0) (193.0 mg, 0.17 mmol) in dioxane (5.0 mL) was added 2 M sodium carbonate solution in water (1.7 mL). The resulting mixture was subjected to microwave irradiation for 2 h at 110° C. The mixture was diluted with ethyl acetate (200 mL), washed with saturated aqueous sodium bicarbonate solution (50 mL×2), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (10% ethyl acetate/hexanes) afforded 2-(2′-hydroxy-biphenyl-3-yl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-sulfonic acid cyclobutylamide (412.1 mg, 53.4%) as a white solid: MS (ESI) M+1=463.1.

Provenance & Evidence