Dibromomethane → 1-(3-Dibenzylamino-2,6-difluoro-phenyl)-2-[1,3]dithietan-2-ylidene-2-pyridin-4-yl-ethanone

Participants

Reaction Steps

To a solution of 1-(3-Dibenzylamino-2,6-difluoro-phenyl)-2-pyridin-4-yl-ethanone (2.14 g, 4.994 mmol) in dry DMSO (22 mL) under nitrogen atmosphere solid potassium carbonate (2.07 g, 15 mmol, 3 eq) was added at room temperature, followed by carbon disulfide (0.9 mL, 15 mmol, 3 eq) and dibromomethane (1.05 mL, 15 mmol, 3 eq). The reaction mixture was stirred at room temperature for 3 hour and then poured into stirred iced water (150 mL). The aqueous phase was extracted with ethyl acetate (3 x 70 mL) and the combined organic layers were washed with water, dried and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (n-hexane/ethyl acetate 7:3 to 6:4) to obtain 1.26 g of 1-(3-dibenzylamino-2,6-difluoro-phenyl)-2-[1,3]dithietan-2-ylidene-2-pyridin-4-yl-ethanone as yellow solid (49%).

Provenance & Evidence