Potassium Carbonate → (S)-3-{4-[2-(4-Cyano-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-ylmethoxy]-phenyl}-hex-4-ynoic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of ethyl (3S)-3-[4-[(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-6-yl)methoxy]phenyl]hex-4-ynoate (0.25 g, 0.57 mmol) and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile (0.14 g, 0.5 mmol) in dioxane (115 mL) is added K2CO3 (0.15 g, 1.134 mmol). The mixture is purged with argon for 30 minutes, Pd(PPh3)4 (0.032 g, 0.027 mmol) is added and the mixture is heated at 100° C. for 5 hours. The reaction mixture is cooled to room temperature, filtered through diatomaceous earth. The filtrate is evaporated under reduced pressure and concentrated to dryness. The crude material is purified by silica gel chromatography (combiflash) eluting with 30% EtOAc/hexane to give the title compound as a brown liquid (0.170 g, 68.75%). LCMS m/z 464 (M+H).

Provenance & Evidence