Potassium Carbonate → HCID 58466218, compound

Participants

Reaction Conditions

Reaction Steps

Combined tetrakis(triphenylphosphine)palladium (54.2 mg, 0.047 mmol), (S)-4′-fluoro-2′-methoxy-7′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (200 mg, 0.47 mmol, prepared as described in Method BB40) and 2-chloro-6-(prop-1-ynyl)pyrazine (93 mg, 0.61 mmol) in a sealable tube and potassium carbonate (1.5 M) (1.6 mL, 2.35 mmol) was added. The tube was sealed and heated at 110° C. in a microwave for 8 min. The reaction solution was diluted with water and extractd by EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc again. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to provide a brown oil that was purified by chromatography through a gold Redi-Sep pre-packed silica gel column using a gradient of 25% to 50% to 80% DCM: MeOH: NH4OH (90:10:1) in 40% EtOAc in hexane to provide (S)-4′-fluoro-2′-methoxy-7′-(6-(prop-1-ynyl)pyrazin-2-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (60 mg, 0.144 mmol, 30.7% yield) as white solid.

Provenance & Evidence