Potassium Carbonate → HCID 57756374, compound

Participants

Reaction Conditions

Reaction Steps

N,N-Dimethylformamide (1.2 ml) and a 2 M aqueous potassium carbonate solution (1 ml) were added to 4-[(2-iodo-6-methyl-3-pyridyl)oxy]-6,7-dimethoxy-quinoline (compound 116) (50 mg), tetrakistriphenylphosphine palladium (70 mg), and 4-(4,4,5,5-tetramethyl-[1,3]dioxolan-2-ylboranyl)-1H-pyrazole (34 mg) under an argon atmosphere, and the mixture was stirred at 70° C. for 4 hr. The reaction solution was cooled to room temperature and was then filtered through Celite. The solvent was removed from the filtrate by distillation under the reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water. The ethyl acetate layer was extracted with 1 N hydrochloric acid. The aqueous layer was then made alkaline by the addition of a 1 N aqueous sodium hydroxide solution and was extracted with ethyl acetate. The ethyl acetate layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using hexane-acetone to give the title compound (19 mg, yield 44%).

Provenance & Evidence