Stannous Chloride → 2-Bromo-5-fluoropyridin-3-amine

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-bromo-5-fluoro-3-nitropyridine (4.42 g, 20 mmol) and SnCl2 (22.56 g, 100 mmol) in EtOH (40 mL) and concentrated HCl (40 mL) was heated at 60° C. for 1 h. The reaction mixture was concentrated under reduced pressure. To the residue was added EtOAc (100 mL) and sat'd aq. NaHCO3 solution (200 mL), and the mixture was filtered with Celite® and extracted with EtOAc (100 mL×3). The organic layer was washed with saturated NaHCO3, water and brine, dried (MgSO4), filtered, and concentrated under reduced pressure to afford 3.1 g (80%) of 2-bromo-5-fluoropyridin-3-amine as a brown solid. MS (ESI): m/z=191.1 [M+1]+.

Provenance & Evidence