Sodium Hydroxide → HCID 178510688, compound

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Reaction Steps

LiAlH4 (0.06 g, 1.5 mmol) and anhydrous diethyl ether (2 mL) were introduced into a volumetric flask. The mixture was cooled with an ice bath and a solution of 4,6-bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile (0.15 g, 0.4 mmol, obtained in example 65) in diethyl ether (1 mL) was added dropwise. THF (2 mL) was added and the mixture was stirred at room temperature overnight. It was cooled with an ice bath and successively water (0.1 mL), THF (0.2 mL), a 15% aqueous NaOH (0.1 mL) and water (0.3 mL) were added. The precipitate obtained was filtered and washed with THF. The solvent of the filtrate was evaporated. The residue obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 71 mg of the title compound in solid form (yield: 47%).

Provenance & Evidence