Potassium Carbonate → HCID 57813261, compound

Participants

Reaction Steps

N-{[3-Bromo-4-(methyloxy)phenyl]methyl}-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide (0.64 g, 0.99 mmol), (3-formylphenyl)boronic acid (0.193 g, 1.29 mmol), potassium carbonate (0.41 g, 2.97 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.058 g, 0.05 mmol) were combined in dioxane (6 mL) and water (2 mL). The mixture was microwaved at 150° C. for 30 min. The reaction mixture was diluted with EtOAc and washed 3× with H2O. The organic phase was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified using CombiFlash on a 40 g column eluted with 0-10% MeOH/CH2Cl2 to give the title compound as a white solid. LC-MS m/z 675.1 (M+H)+, 1.85 min (ret time); mp 118-121° C.; analytical HPLC shows 100% purity, (ret time 13.204 min).

Provenance & Evidence