Acetone → Ethyl 1-(1-methylethyl)-6-[4-(methylsulfonyl)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Participants

Reaction Steps

Oxone (1712 mg, 2.79 mmol) was added to a solution of ethyl 1-(1-methylethyl)-6-[4-(methylthio)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (330 mg, 0.928 mmol) in acetone (6 mL) and water (2 mL), and the reaction mixture was stirred for 6 h. The reaction mixture was quenched with water (10 mL) and then neutralized with NaHCO3 solution. The mixture was extracted with EtOAc (3×) and the combined extracts dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified using column chromatography (Silica gel, 0 to 100% EtOAc/hexanes) to give 295 mg (82%) of product. LCMS E-S (M+H)=388.1. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.54 (t, J=7.2 Hz, 3H), 1.67-1.69 (d, J=6.8 Hz, 6H), 3.14 (s, 3H), 4.58 (q, J=7.2 Hz, 2H), 5.48 (spt, J=6.7 Hz, 1H), 8.06-8.18 (m, 2H), 8.29 (s, 1H), 8.39-8.44 (m, 2H), 8.47 (s, 1H).

Provenance & Evidence