Acetonitrile → HCID 71253911, compound

Participants

Reaction Steps

To a mixture of 5-bromo-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine (90.0 mg, 0.304 mmol), 5-fluoropyridin-3-ylboronic acid (128.6 mg, 0.9124 mmol) and 1,1′-Bis(diphenylphosphino)ferrocenepalladium (II) chloride (37.2 mg, 0.0456 mmol) in Acetonitrile (2.86 mL, 54.7 mmol) was added 1.0 M of Potassium acetate in Water (0.456 mL) and 1.0 M of Sodium carbonate in Water (0.456 mL). The reaction mixture was irradiated in microwave at 125° C. for 20 min. The reaction was filtered thru celite and concentrated. The crude product was purified by silica gel column using ethyl acetate/heptane to give 5-(5-fluoropyridin-3-yl)-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine which was dissolved in 12M HCl (1.30 mL, 15.6 mmol) and Methanol (13.0 mL). The reaction mixture was stirred at RT (room temperature) for 18 h. The reaction was concentrated and then submitted for rHPLC to give 123 (27.9 mg, 40.2% yield). ESI MS m/z=229.1 (M+1). 1H NMR (400 MHz, DMSO) δ 9.25 (s, 1H), 9.08 (s, 1H), 8.62-8.49 (m, 2H), 8.47-8.30 (m, 1H), 2.60 (s, 3H)

Provenance & Evidence