Potassium Cyanide → HCID 21897310, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-(5-bromo-pyrazin-2-yl)-2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide (616.0 mg, 1.266 mmol), potassium cyanide (210.0 mg, 3.225 mmol), tetrakis(triphenylphosphine)palladium(0) (30.0 mg, 0.026 mmol), copper(I) iodide (605.0 mg, 3.177 mmol), and 18-crown-6 (33.0 mg, 0.125 mmol) in anhydrous N,N-dimethylformamide (6 mL) was heated at 150° C. under nitrogen. After 2.75 h, the mixture was allowed to cool to 25° C. The mixture was then concentrated to remove solvent. The residue was diluted with methylene chloride and ethyl acetate and then filtered through a pad of celite. The celite pad was then washed well with ethyl acetate and methylene chloride. The filtrate was then concentrated in vacuo and absorbed onto silica gel (Merck Silica gel 60, 230–400 mesh). Biotage chromatography (FLASH 40L, Silica, 1/3 to 1/1 ethyl acetate/hexanes) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-N-(5-cyano-pyrazin-2-yl)-3-cyclopentyl-propionamide (402.3 mg, 73.4%) as an off-white foam: (ES)+-HRMS m/e calcd for C20H21ClN4O3S (M+H)+ 433.1096, found 433.1101.

Provenance & Evidence