Water → 3-(6-fluoro-5-methylpyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine

Participants

Reaction Conditions

Reaction Steps

A microwave reaction vial was charged with 3-(5-chloro-6-fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine (387.1 mg, 0.8489 mmol), methyl boronic acid (254.1 mg, 4.245 mmol), 1,1′-Bis(diphenylphosphino)ferrocenepalladium (II) chloride (69.3 mg, 0.085 mmol), 1.00 M of Potassium acetate in Water (1.27 mL, 1.27 mmol), 1.00 M of Sodium carbonate in Water (1.27 mL, 1.27 mmol), and Acetonitrile (10 mL). The reaction mixture was heated under microwave at 150° C. for 5 minutes. Added another 5 equivalences of Methyl boronic acid and continue heated under microwave at 150° C. for 3 minutes. The same procedure was repeated one more times. The mixture was concentrated, and the residue was purified on silica eluted with 0 to 100% EtOAc in Heptane to afford 3-(6-fluoro-5-methylpyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine (311.7 mg, 84%).

Provenance & Evidence