Dimethylformamide → HCID 11755068, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of the N-(5-bromo-pyrazin-2-yl)-2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide (94 mg, 0.19 mmol), mercaptoethanol (0.031 mL, 0.44 mmol), and tetrakis(triphenylphosphine)palladium(0) (111 mg, 0.097 mmol) in anhydrous N,N-dimethylformamide (0.5 mL) was heated at 120° C. in a sealed tube. After 3 h, the mixture was allowed to cool to 25° C., diluted with water, and then extracted with diethyl ether. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck silica gel 60, 230–400 mesh, 55% ethyl acetate/hexanes) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2-hydroxy-ethylsulfanyl)-pyrazin-2-yl]-propionamide (58 mg, 62%) as a light brown foam: mp=78–81° C.; (ES)+-HRMS m/e calcd for C21H27ClN3O4S2 (M+H)+ 484.1126, found 484.1131.

Provenance & Evidence