Potassium Carbonate → HCID 52914483, compound

Participants

Reaction Steps

5-[(5-Bromo-3-fluoropyridin-2-yl)methyl]-6,9-difluoro-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one (Example 103, 63 mg, 0.13 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (45 mg, 0.21 mmol, 1.7 equiv), potassium carbonate (52 mg, 0.38 mmol, 3 equiv), palladium(II) acetate (5.7 mg, 0.025 mmol, 0.2 equiv) and 2-dicyclohexylphosphino-2′,4′,6′-tri-iso-propyl-1,1′-biphenyl (28 mg, 0.058 mmol, 0.46 equiv) were combined in dimethylsulfoxide (0.9 mL) and water (0.2 mL). The mixture was sparged under an atmosphere of nitrogen, the vessel was sealed and placed into a preheated oil bath at 88° C. for 4 hours. The mixture was cooled to ambient temperature, poured into water (25 mL) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed once with water (10 mL) and brine (10 mL), dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (eluting with 98:2; chloroform:methanol), providing the titled compound: high resolution mass spectrometry (ES+) m/z 505.1385 [(M+H)+; calculated for C26H17F4N6O: 505.1395].

Provenance & Evidence