1,2-Dimethoxyethane → 6-(4-Fluorophenyl)-2-methyl-5-(4-pyridyl)-4-[5-(3-pyridyl)thien-2-yl]pyrazolo[3,4-b]pyridine

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-(5-bromothien-2-yl)-6-(4-fluorophenyl)-2-methyl-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine (0.10 g, 0.2 mmol, obtained in example 188), 3-pyridylboronic acid (0.04 g, 0.3 mmol), K2CO3 (0.06 g, 0.4 mmol), Pd(PPh3)4 (0.017 g, 0.01 mmol), 1,2-dimethoxyethane (1.31 mL) and water (0.04 mL) was heated at 80° C. under argon atmosphere overnight. It was allowed to cool and diluted with CHCl3 and water. The combined organic phases were dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 35 mg of the desired compound (yield: 50%).

Provenance & Evidence