Sodium Carbonate → 4-(1H-pyrazol-4-yl)-1-trityl-1H-pyrazolo[3,4-b]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-iodo-1-trityl-pyrazolo[5,4-b]pyridine (1.404 g, 2.880 mmol), 444,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-pyrazole (950 mg, 4.896 mmol) and tetrakis(triphenylphosphine)palladium(0) (166.4 mg, 0.1440 mmol) in DME (20 mL) was treated with Na2CO3 (5.559 g, 5.040 mL of 2 M, 10.08 mmol) and heated in the microwave for 60 minutes at 150° C. The reaction mixture was diluted with EtOAc and water and the layers separated. The organics were dried (MgSO4), filtered and concentrated and purified by column chromatography (1:1 Petroleum ether/EtOAc moving to EtOAc to) give the pure compound as a white solid (597 mg, 49% Yield). 1H NMR (DMSO, 400 MHz) δ 6.25 (1H, m), 7.20-7.25 (15H, m), 7.33 (1H, m), 7.65 (2H, m), 8.19 (1H, m), 8.71 (1H, s), 8.60 (1H, br s); MS (ES+) 428.18

Provenance & Evidence