Stannous chloride dihydrate → HCID 67466807, compound

Temperature

80 °C

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+).

1. temperatureThe mixture was cooled to RT
2. customthe solvent was removed in vacuo and crude residue
3. additionEtOAc (50 mL) was added to the resultant white suspension
4. stirringthe mixture was stirred for few minutes
5. filtrationIt was filtered though a Celite® pad which
6. washwas washed with EtOAc (4×5 mL), and water (3×4 mL)
7. customThe organic layer was separated
8. washwas washed with brine
9. dry with materialdried (Na2SO4)
10. concentrationconcentrated
11. customto afford crude product which
12. customwas purified by silica gel chromatography (EtOAc-hexanes)

ORD record

ord-5811ccb607d547a296774fd1a44ef15d

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569319B2