Ammonia → 3-(Aminomethyl)-5-bromopyridine

3-Bromo-5-hydroxymethylpyridine (1.1 g, 5.8 mmol) was added to thionyl chloride (5 mL) at 0° C. under nitrogen over 5 min. The solution was stirred at room temperature for 1 h, re-cooled to 0° C., and dry ether (40 mL) was added. The resulting solid was filtered off, washed with ether and added to a stirred solution of ammonia (28%, 30 mL) and ethyl alcohol (40 mL) at 0° C. The solution was then stirred at room temperature for 20 h. The solvent was removed by rotary evaporation and the crude material partitioned between sodium hydroxide (2N, 30 mL) and dichloromethane (60 mL). The organic layer was dried (Na2SO4), the solvent removed by rotary evaporation and the residue purified by flash chromatography, using CHCl3: ethanol: concentrated aqueous ammonia solution (100:6:1) as eluent, to afford (5-bromo-3-pyridyl)methylamine (785 mg, 72% yield).

1. temperaturere-cooled to 0° C.
2. filtrationThe resulting solid was filtered off
3. washwashed with ether
4. additionadded to a stirred solution of ammonia (28%, 30 mL) and ethyl alcohol (40 mL) at 0° C
5. stirringThe solution was then stirred at room temperature for 20 h
6. customThe solvent was removed by rotary evaporation
7. customthe crude material partitioned between sodium hydroxide (2N, 30 mL) and dichloromethane (60 mL)
8. dry with materialThe organic layer was dried (Na2SO4)
9. customthe solvent removed by rotary evaporation
10. customthe residue purified by flash chromatography

ORD record

ord-7fa22c6d09ba4bcd8e381cfe7d742e1c

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07214686B2