Stannous chloride dihydrate → 5-Bromo-2-(2,2-dimethylmorpholino)pyridin-3-amine

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 4-(5-bromo-3-nitropyridin-2-yl)-2,2-dimethylmorpholine (2.22 g, 7.03 mmol) in EtOAc (30 mL) was added tin(II) chloride dihydrate (8.94 g, 39.6 mmol) in portions. Upon complete addition of the reducing agent, the mixture was carefully heated to 90° C. After 1 h, the reaction was cooled to rt, then washed with 1M NaOH, water, and brine. After drying over anhydrous sodium sulfate and filtration, the organic solvent was removed under reduced pressure. The residue was purified with silica gel chromatography (0-35% EtOAc in hexanes) to provide a colorless film as 5-bromo-2-(2,2-dimethylmorpholino)-pyridin-3-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.59 (1H, d, J=2.2 Hz), 7.13 (1H, d, J=2.3 Hz), 5.10 (2H, s), 3.83 (2H, m), 2.90 (2H, m), 2.77 (2H, s), 1.24 (6H, s).

Provenance & Evidence