Potassium Carbonate → HCID 88996204, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, a solution of 4-chloro-3-methyl-2-oxo-2,3-dihydro-thiazole-5-carbaldehyde (33b) (500 mg, 2.82 mmol), potassium carbonate (390 mg, 2.82 mmol), palladium diacetate (100 mg, 0.48 mmol), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman (732 mg, 2.82 mmol) and tetrabutylammonium bromide (910 mg, 2.82 mmol) in ethanol (7 mL) and water (10 mL) was stirred at 70° C. for 3 hours. The mixture was then cooled at room temperature and diluted with ethyl acetate (30 mL) and water (30 mL). The organic layer was washed with water (30 mL), brine (30 mL), dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20) to afford the desired product as a white solid (270 mg, 0.98 mmol, 35%).

Provenance & Evidence