Cesium carbonate → HCID 52914606, compound

Participants

Reaction Steps

5-[(6-Chloropyridin-3-yl)methyl]-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one (Example 225, 40 mg, 0.10 mmol), bis(tri-tert-butylphosphine)palladium(0) (5.0 mg, 0.010 mmol, 0.1 equiv), cesium carbonate (0.20 mL, 1 M aqueous, 0.20 mmol, 2 equiv) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (35 mg, 0.17 mmol, 1.7 equiv) were suspended in tetrahydrofuran (1 mL) and the mixture was irradiated (high setting) for 10 minutes at 140° C. The mixture was cooled to ambient temperature, the organic layer removed, stirred with Quadrapure® (40 mg, 1 wt equiv) for 1 hour, filtered and purified by reverse phase HPLC (80:20 to 5:95; water containing 0.1% trifluoroacetic acid:acetonitrile containing 0.1% trifluoroacetic acid), providing the titled compound: 1H-NMR (400 MHz, d6-DMSO) δ 9.16 (1H, s), 8.65 (1H, d, J=2.2 Hz), 829 (1H, s), 8.20 (1H, dd, J=7.8, 1.4 Hz), 7.99 (1H, s), 7.83 (1H, d, J=8.7 Hz), 7.76 (1H, dd, J=8.2, 2.0 Hz), 7.66-7.58 (3H, m), 7.54 (1H, t, J=7.5 Hz), 7.48-7.37 (2H, m), 7.34 (1H, td, J=7.7, 1.5 Hz), 5.76 (2H, s), 3.87 (3H, s) ppm; low resolution mass spectrometry (ES+) m/z 451.0 [(M+H)+; calculated for C26H20FN6O: 451.2].

Provenance & Evidence