Potassium Carbonate → HCID 68558982, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 2,2,4,4-tetramethyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3,4,7,8,9-hexahydro-1H-cyclopenta[h]quinolin-3-one-1-carboxylate (1.2 g) obtained in Example 1, 9) in isopropanol (11 ml) were added 4-bromo-3-[1,3]dioxolan-2-yl-5-methylisoxazole (500 mg), 2.0 M aqueous potassium carbonate solution (3.2 ml) and tetrakis(triphenylphosphine)palladium(0) (250 mg), and the mixture was stirred at 80° C. for 16 hr. The reaction solution was diluted with water and ethyl acetate, the mixture was filtered through celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to normal phase chromatography (elution solvent hexane-ethyl acetate=6:1) to give tert-butyl 6-(3-[1,3]dioxolan-2-yl-5-methylisoxazol-4-yl)-2,2,4,4-tetramethyl-2,3,4,7,8,9-hexahydro-1H-cyclopenta[h]quinolin-3-one-1-carboxylate (410 mg, 32%).

Provenance & Evidence