Cesium carbonate → HCID 57899418, compound

Participants

Reaction Conditions

Reaction Steps

In the last step, 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 (5, 0.5 g, 0.89 mmol) in N,N-dimethylformamide (15 mL) is degassed with argon for 0.5 h. Then 2-amino-5-bromopyridine (0.21 g, 1.22 mmol), cesium carbonate (0.53 g, 1.618 mmol), Pd(dppf)2Cl2 (0.03 g, 0.04 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 6 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 preparative HPLC to afford N-{3-[6-[4-(6-amino-pyridin-3-yl)-phenyl]-5-(4-chloro-phenyl)-4-oxo-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-phenyl}-methane sulfonamide, as a pale yellow solid. 1H NMR (CD3OD, 400 MHz) δ 8.34 (s, 1H), 8.27 (s, 1H), 8.15 (m, 2H), 7.90 (d, 1H), 7.60 (m, 5H), 7.4 (m, 2H), 7.34 (m, 2H), 7.2 (d, 1H), 7.0 (d, 1H), 2.99 (s, 3H); LC-MS calculated for C29H22ClN7O3S (M+H+) 584.1, found 584.1.

Provenance & Evidence