Cesium carbonate → HCID 68815114, compound

Participants

Reaction Steps

Dissolve 2-acetyl-6-chloro-isonicotinic acid methyl ester (300 mg, 1.4 mmol), palladium (II) acetate (16 mg, 0.07 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (46 mg, 0.07 mmol) and cesium carbonate (781 mg, 2.1 mmol) in anhydrous toluene (3 mL) in a previously degassed sealed vessel. Flush the mixture with nitrogen gas. Add (S)-(+)-sec-butylamine (0.16 mL, 1.68 mmol) to the solution under nitrogen and heat the sealed mixture overnight at 100° C. Cool the reaction to room temperature. Dilute with diethyl ether and filter through a filtering agent. Concentrate the filtrate and purify (silica gel chromatography, eluting with 0:100 to 5:95 ethyl acetate:hexanes) to give the title compound as a solid (17%).

Provenance & Evidence