Potassium Carbonate → HCID 46896613, compound

Participants

Reaction Steps

5-[(6-Bromopyridin-3-yl)methyl]-2-(2-methylphenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one [(Example 22) 74 mg, 0.17 mmol] was dissolved in dimethyl sulfoxide (1 mL) and treated with 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (59 mg, 0.28 mmol, 1.7 equiv), 2-(dicyclohexylphosphino)-2′,4′,6′-tri-iso-propylbiphenyl (X-PHOS, 36 mg, 0.076 mmol, 0.46 equiv), palladium(II)acetate (8.0 mg, 0.033 mmol, 0.2 equiv), and an aqueous solution (0.2 mL) of potassium carbonate (69 mg, 0.50 mmol, 3.0 equiv). The mixture was placed into an oil bath preheated at 80° C. for 30 minutes, cooled to ambient temperature, poured into water and extracted twice with ethyl acetate. The combined organic extracts were washed once with water and brine, dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 94:6; chloroform:methanol), providing the titled compound: 1H-NMR (400 MHz, CDCl3) δ 8.63 (1H, s), 8.31 (1H, d, J=7.5 Hz), 7.93 (1H, s), 7.91 (1H, s), 7.68-7.53 (4H, m), 7.47-7.41 (2H, m), 7.38-7.31 (3H, m), 5.84 (2H, s), 3.96 (3H, s), 2.38 (3H, s) ppm; high resolution mass spectrometry (ES+) m/z 448.1885 [(M+H)+; calculated for C26H22N7O: 448.1880].

Provenance & Evidence