Hydrochloric Acid → (1R)-1-{4-[3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridin-2-yl]phenyl}ethanamine

Participants

Reaction Conditions

Reaction Steps

A solution of N-{1-[4-(5-chloro-3-phenyl-1,6-naphthyridin-2-yl)phenyl]ethyl}-2-methylpropane-2-sulfinamide (2-3, 0.10 g, 0.22 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (0.12 g, 0.39 mmol), cesium carbonate (0.21 g, 0.64 mmol) and bis(tri-t-butylphosphine)palladium(0) (0.013 g, 0.025 mmol) in a 7/3/1 mixture of dioxane/ethanol/water (3 mL) was heated to 100° C. in a microwave for 10 minutes. The crude reaction mixture was treated with HCl in ether (3 mL). After 30 minutes, the reaction was concentrated and purified by reverse phase chromatography (5-95% acetonitrile/water/0.1% TFA, Sunfire C18) to give (1R)-1-{4-[3-phenyl-5-(1H-pyrazol-4-yl)-1,6-naphthyridin-2-yl]phenyl}ethanamine (2-4) as a white solid. MS (M+H)+: 428

Provenance & Evidence