Stannous chloride dihydrate → HCID 67466807, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(2,5-difluoro-4-nitrophenoxy)-3-iodopyridin-2-amine (0.78 g, 1.78 mmol) in EtOH (15 mL) added tin(II) chloride dihydrate (2.0 g, 8.93 mmol) and the reaction mixture was stirred at 80° C. for 3 h. The mixture was cooled to RT, the solvent was removed in vacuo and crude residue was basified with NaHCO3 solution (40 mL). EtOAc (50 mL) was added to the resultant white suspension and the mixture was stirred for few minutes. It was filtered though a Celite® pad which was washed with EtOAc (4×5 mL), and water (3×4 mL). The organic layer was separated and was washed with brine, dried (Na2SO4) and concentrated to afford crude product which was purified by silica gel chromatography (EtOAc-hexanes) to afford 4-(4-amino-2,5-difluorophenoxy)-3-iodopyridin-2-amine as an off-white solid (0.33 g, 51% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.69 (d, J=5.6 Hz, 1H), 7.12 (dd, J=11.2 Hz, 7.6 Hz, 1H), 6.69 (dd, J=12.0 Hz, 8.0 Hz, 1H), 6.13 (s, 2H), 5.74 (d, J=5.6 Hz, 1H), 5.47 (s, 2H); MS (ESI) m/z: 364.0 (M+H+).

Provenance & Evidence