Stannous chloride dihydrate → 4-(3-Bromopyridin-4-yloxy)-2,5-difluorobenzenamine

Participants

Reaction Conditions

Reaction Steps

3-Bromo-4-(2,5-difluoro-4-nitrophenoxy)pyridine (0.414 g, 1.25 mmol) was dissolved in EtOH (30 ml). Tin (II) chloride dihydrate (1.129 g, 5.00 mmol) was added and the mixture was heated at 80° C. for 4 h. The solvent was removed under reduced pressure and the residue quenched with sat. NaHCO3 (aq). The mixture was diluted with EtOAc and filtered through Celite®. The Celite bed was washed with water (2×) and EtOAc (2×). The filtrate was extracted with EtOAc (2×). The combined organic extracts were dried and evaporated to yield 4-(3-bromopyridin-4-yloxy)-2,5-difluorobenzenamine (0.42 g, 112% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.68 (s, 1H), 8.33 (d, 1H), 7.28-7.23 (m, 1H), 6.76-6.71 (m, 2H), 5.56 (br s, 2H); MS (ESI) m/z: 301.0 (M+H+).

Provenance & Evidence