Sodium Hydroxide → 1-(5-Bromopyridin-2-yl)ethan-1-amine

Participants

Reaction Steps

To a stirred solution of 5-bromo-pyridine-2-carbonitrile (1 g, 5.46 mmol) in dry THF (10 mL) was added dropwise MeMgBr (2.03 mL, 6.09 mmol, 3M in THF) at −20° C. under N2 atmosphere. After the addition, the reaction mixture was stirred at room temperature for 30 mins. The suspension was then treated with methanol (20 mL) and NaBH4 (0.4 g, 13.3 mmol). The reaction was stirred at room temperature for 10 hrs and then poured into H2O (10 mL) and aqueous NaOH (2M, 10 mL), extracted with EtOAc (50 mL×2). The combined organic layers were washed with brine (50 mL×3), dried over Na2SO4 and concentrated in vacuum. The residue was purified by a silica gel column chromatography (petroleum:EtOAc 3:1) to give 1-(5-bromo-pyridin-2-yl)-ethylamine (0.65 g, 59%) as a yellow liquid.

Provenance & Evidence