Stannous chloride dihydrate → 5-Bromo-6'-methoxy-2,3'-bipyridin-3-amine

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 5-bromo-6′-methoxy-3-nitro-2,3′-bipyridine (0.34 g, 1.10 mmol) in EtOAc (10 mL) was added tin(II) chloride dihydrate (1.26 g, 5.57 mmol) in portions. Upon complete addition of the reducing agent, the mixture was carefully heated to 70° C. After 19 h, the reaction was cooled to rt and diluted with EtOAc, then washed with 1M NaOH, water, and brine. After drying over anhydrous sodium sulfate, filtration, and concentration, the residue was identified as mostly 5-bromo-6′-methoxy-2,3′-bipyridin-3-amine. 1H NMR (500 MHz, CDCl3) δ ppm 8.50 (1H, d, J=2.4 Hz), 8.18 (1H, d, J=2.0 Hz), 7.90 (1H, dd, J=8.6, 2.4 Hz), 7.26 (1H, m), 6.88 (1H, d, J=8.6 Hz), 4.07 (5H, m).

Provenance & Evidence