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

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.

1. additionAfter the addition
2. stirringThe reaction was stirred at room temperature for 10 hrs
3. extractionextracted with EtOAc (50 mL×2)
4. washThe combined organic layers were washed with brine (50 mL×3)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated in vacuum
7. customThe residue was purified by a silica gel column chromatography (petroleum:EtOAc 3:1)

ORD record

ord-8bc5f4967fda4d8aa91dec91c9861c59

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916593B2