Cesium carbonate → Ethyl 4-[[6-(4-Hydroxy-4-Methyl-1-Piperidyl)-3-Methyl-Pyridine-2-carbonyl]amino]-3,5-dimethyl-benzoate

Participants

Reaction Steps

To a solution of ethyl 4-[(6-chloro-3-methyl-pyridine-2-carbonyl)amino]-3,5-dimethyl-benzoate (275 mg, 792.93 mmoles), 4-methylpiperidin-4-ol (120 mg, 1.04 mmol) and Cs2CO3 (0.8 g, 2.46 mmol) in 1,4-dioxane (6 ml) is added Pd(OAc)2 (27 mg, 120.26 μmoles) followed by racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (54 mg, 86.72 moles). The reaction mixture is purged with nitrogen for 5 minutes and then heated to reflux. After 2 hours, the reaction is cooled to ambient temperature and diluted with ammonium chloride and extracted twice with EtOAc. The combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (silica gel) using 0-70% ethyl acetate in hexane to afford the title compound as a yellow oil (0.27 g, 80%). Mass spectrum (m/z): 426.2 (M+1).

Provenance & Evidence