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 (776.9 mg, 2.50 mmol) in EtOAc (25 mL) was added tin(II) chloride dihydrate (2.83 g, 12.56 mmol) in portions. Upon complete addition of the reducing agent, the mixture was carefully heated to 90° C. After 2 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 light tan solid was identified as 5-bromo-6′-methoxy-2,3′-bipyridin-3-amine. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.42 (1H, dd, J=2.4, 0.7 Hz), 7.98 (2H, m), 7.34 (1H, d, J=2.0 Hz), 6.90 (1H, dd, J=8.6, 0.7 Hz), 5.49 (2H, s), 3.90 (3H, s).

Provenance & Evidence