Bromine → HCID 86657965, compound

Participants

Reaction Steps

To a solution of potassium thiocyanate (4.31 g, 44.4 mmol) in acetic acid (15 ml) was added a solution of N-[3-[(5-aminopyridin-2-yl)(methyl)amino]phenyl]-2,2,2-trifluoroacetamide (3.46 g, 11.1 mmol) in acetic acid (10 mL), and the mixture was stirred at room temperature for 20 min. To this solution was added dropwise a solution of bromine (1.95 g, 12.2 mmol) in acetic acid (10 mL), and the mixture was stirred at room temperature for 16 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (140 mL)/tetrahydrofuran (70 mL), and washed with aqueous sodium hydrogen carbonate solution (70 mL) and saturated brine (50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→0/100) to give the title compound (829 mg, 20%) as a violet powder.

Provenance & Evidence