Cesium carbonate → HCID 57899357, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-(3-{5-(4-chloro-phenyl)-4-oxo-6-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl}-phenyl)-methane sulfonamide (prepared as described in example 35, 0.50 g, 0.81 mmol) in N,N-dimethylformamide (20 mL) is degassed with argon for 0.5 h. Then 2-iodopyridazine (0.25 g, 1.2 mmol), cesium carbonate (0.527 g, 1.61 mmol), Pd(dppf)2Cl2 (0.06 g, 0.08 mmol) are added and the resulting solution is degassed with argon for 0.5 h. The reaction mixture is then heated at 100° C. for 3 h. The reaction mixture is cooled to rt and diluted with water and extracted with ethyl acetate (3×). The combined organic layer is washed with brine, dried over Na2SO4, concentrated, and purified by column chromatography to afford N-{3-[5-(4-chloro-phenyl)-4-oxo-6-(4-pyridazin-3-yl-phenyl)-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-phenyl}-methane sulfonamide (0.155 g, 34% yield). 1H NMR (DMSO-dg, 400 MHz) δ 10.15 (br, 1H), 9.22 (m, 1H), 8.52 (s, 1H), 8.22 (d, 1H), 8.06 (m, 3H), 7.83 (m, 1H), 7.81 (m, 1H), 7.62 (m, 2H), 7.52 (m, 1H), 7.42-7.48 (m, 4H), 7.20 (m, 1H), 3.02 (s, 3H); LC-MS calculated for C28H20ClN7O3S (M+H+) 570.1, found 569.9.

Provenance & Evidence