Pyridine → HCID 22315194, compound

Participants

Reaction Conditions

Reaction Steps

Triphenylphosphine (238 mg, 0.91 mmol) was dissolved in methylene chloride (10 mL) and cooled to 0° C. To this solution was added N-bromosuccinimide (183 mg, 1.03 mmol) and was stirred at 0° C. until it was completely dissolved and became light purple in color. The 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (200 mg, 0.61 mmol) was then added and it was stirred at 0° C. for 20 min and then warmed to 25° C. and stirred for 30 min. After such time 2-aminopyridine (85 mg, 0.91 mmol) and pyridine (0.088 mL, 1.09 mmol) were added and it was stirred at 25° C. for 16 h. The reaction was then diluted with water (10 mL) and then extracted with methylene chloride (3×15 mL). The organic layers were then combined and dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 60/40 hexanes/ethyl acetate) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-pyridin-2-yl-propionamide (210 mg, 85%) as a colorless oil: EI-HRMS m/e calcd for C20H23N2O3SCl (M+) 406.1118, found 406.1120.

Provenance & Evidence