Pyridine → HCID 10136295, compound

Participants

Reaction Conditions

Reaction Steps

A solution of triphenylphosphine (120 mg, 0.46 mmol) in methylene chloride (5 mL) was cooled to 0° C. and then slowly treated with N-bromosuccinimide (92 mg, 0.52 mmol). The reaction mixture was stirred at 0° C. until the reaction mixture became homogeneous. The resulting light purple reaction mixture was then treated with (E)-2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-acrylic acid (100 mg, 0.30 mmol), and the reaction mixture was stirred at 0° C. for 20 min. The reaction mixture was then allowed to warm to 25° C. where it was stirred for 30 min. After such time, the reaction mixture was treated with 2-aminothiazole (46 mg, 0.46 mmol) and pyridine (0.044 mL, 0.55 mmol), and the resulting reaction mixture was stirred at 25° C. for 16 h. The reaction was then diluted with water (10 mL) and extracted with methylene chloride (3×15 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 70/30 hexanes/ethyl acetate) afforded the (E)-2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-thiazol-2-yl-acrylamide (63 mg, 50%) as a yellow oil: EI-HRMS m/e calcd for C18H19ClN2O3S2 (M+) 410.0526, found 410.0529.

Provenance & Evidence