Sodium Carbonate → 5-Bromo-3-phenyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazolo[3,4-b]pyridine

Participants

Reaction Conditions

Reaction Steps

PdCl2(dppf) dichloromethane adduct (0.017 g, 0.02 mmol) was added to a suspension of 5-bromo-3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridine (0.185 g, 0.41 mmol), phenylboronic acid (0.050 g, 0.41 mmol) and Na2CO3 (0.064 g, 0.61 mmol) in dimethylether (“DME”)/EtOH/H2O (5:2:1, 8 mL). The reaction mixture was purged with argon for 10 minutes and then heated to 90° C. under argon for 2 hours. The reaction mixture was cooled to room temperature and concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (50:1) to give 5-bromo-3-phenyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridine (0.080 g, 49%) as an oil.

Provenance & Evidence