Pyridine → HCID 67341642, compound

Participants

Reaction Steps

To a solution of 0.350 g (1.02 mmol) of (5′-bromo-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-acetic acid in dimethylformamide (5 mL) is added 0.450 g (1.19 mmol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate followed by 0.380 mL (2.13 mmol) of pyridine. The mixture is stirred at room temperature for 1 hour then 0.225 mg (1.97 mmol) of N-methylhomopiperizine is added and the mixture is stirred at room temperature for 1 h. The mixture is diluted with water and extracted with ethyl acetate. The combined organic phase is washed with water followed by brine then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography to provide 0.310 g (69.2%) of 2-(5′-bromo-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-1-(4-methyl-[1,4]diazepan-1-yl)-ethanone as an orange oil.

Provenance & Evidence