1,4-Cyclohexadiene → HCID 178423003, compound

Participants

Reaction Steps

To a solution of 2.12 g (3.2 mmol) of tert-butyl 4-(4-(6-(4-(benzyloxy)-3-methylphenyl)-5-cyano-3-(furan-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-yl)phenyl)piperazine-1-carboxylate in a MeOH/CH2Cl2 mixture are added 0.41 g (0.38 mmol) of 10% Pd/C and 3 ml (2.57 g, 32.0 mmol) of 1,4-cyclohexadiene. The mixture is refluxed for 18 h, then 0.41 g (0.38 mmol) of 10% Pd/C and 3 ml (2.57 g, 32.0 mmol) of 1,4-cyclohexadiene are added, and the mixture is refluxed for an additional 24 h, 0.41 g (0.38 mmol) of 10% Pd/C and 3 ml (2.57 g, 32.0 mmol) of 1,4-cyclohexadiene are added and the mixture is again refluxed for 24 h. The mixture is then concentrated, dissolved in dichloromethane, filtered on Celite, then concentrated. The residue is purified by chromatography on silica (MeOH gradient in dichloromethane: 0 to 3%) to give 0.92 g (50%) of tert-butyl 4-(4-(5-cyano-3-(furan-2-yl)-6-(4-hydroxy-3-methylphenyl)-1H-pyrazolo[3,4-b]pyridine-4-yl)phenyl)piperazine-1-carboxylate in the form of yellow crystals.

Provenance & Evidence