Cesium fluoride → HCID 46897012, 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), 77 mg, 0.17 mmol] and 4-(tributylstannyl)thiazole (77 mg, 0.21 mmole, 1.2 equiv) were dissolved in degassed N,N-dimethylformamide (1 mL) and treated with cesium fluoride (52 mg, 0.34 mmol, 2 equiv), copper(I)iodide (13 mg, 0.069 mmol, 0.4 equiv), and tetrakis(triphenylphosphine)palladium(0) (40 mg, 0.035 mmol, 0.2 equiv). The mixture was stirred at ambient temperature for one hour, diluted with ethyl acetate (15 mL) and filtered. The filtrate was concentrated in vacuo and the residue was purified by preparative reverse phase HPLC (15:85 to 65:35; acetonitrile containing 0.01% trifluoroacetic acid:water containing 0.01% trifluoroacetic acid), providing the titled compound: 1H-NMR (400 MHz, CDCl3) δ 9.13 (1H, s), 8.95 (1H, s), 8.50 (1H, s), 8.35 (2H, br d, J=7.9 Hz), 8.08 (1H, d, J=8.5 Hz), 7.73-7.60 (3H, m), 7.45 (1H, br s), 7.39-7.31 (3H, m), 5.97 (2H, s), 2.73 (3H, s) ppm; low resolution mass spectrometry (ES+) m/z 451.3 [(M+H)+; calculated for C25H19N6OS: 451.3].

Provenance & Evidence