Ammonium Chloride → Tert-butyl (4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)carbamate

Participants

Reaction Steps

A solution of tert-butyl (4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)carbamate (1.6 g, 4.81 mmol) in MeOH (25 mL) and THF (25 mL) was treated with NH4Cl (7.73 g, 144 mmol) followed by the portion-wise addition of zinc dust (3.15 g, 48.1 mmol) and stirred at RT overnight. The solids were removed via filtration through diatomaceous earth, washed with THF and EtOAc and the filtrate concentrated to dryness. The residue was suspended in THF, sonicated, the solids removed via filtration and the filtrate concentrated to dryness. The material was suspended in DCM, washed with water, the aqueous layer back-extracted with DCM and the combined organics were dried over Na2SO4 and concentrated to dryness to afford tert-butyl (4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)carbamate (1.6 g, 110%). 1H NMR (400 MHz, DMSO-d6): δ 9.76 (s, 1H), 8.06 (d, J=5.7 Hz, 1H), 7.78 (d, J=2.9 Hz, 1H), 7.26-7.25 (m, 2H), 6.55-6.48 (m, 2H), 6.01 (s, 2H), 1.40 (s, 9H); MS (ESI) m/z: 303.1 (M+H+).

Provenance & Evidence