Ammonium Chloride → HCID 90402432, compound

Participants

Reaction Steps

A 0° C. solution of 2-methyl-5-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)thiazole (0.191 g, 0.608 mmol) in THF (3 mL) and MeOH (3 mL) was treated with NH4Cl (1.3 g, 24.31 mmol) followed by the slow addition of zinc dust (0.397 g, 6.08 mmol), the mixture allowed to warm to RT and stirred for 2 h. The mixture was treated with THF, the solids removed via filtration through diatomaceous earth, washed well with THF, the filtrate treated with EtOAc, washed with 1:1 brine/satd. NaHCO3, dried over Na2SO4 and concentrated to dryness to afford 5-((2-(2-methylthiazol-5-yl)pyridin-4-yl)oxy)pyridin-2-amine (164 mg, 95%). 1H NMR (400 MHz, DMSO-d6): δ 8.34 (d, J=5.8 Hz, 1H), 8.28 (s, 1H), 7.82 (d, J=2.9 Hz, 1H), 7.50 (d, J=2.4 Hz, 1H), 7.29 (dd, J=8.9, 3.0 Hz, 1H), 6.67 (dd, J=5.8, 2.4 Hz, 1H), 6.51 (d, J=8.9 Hz, 1H), 6.03 (s, 2H), 2.64 (s, 3H); MS (ESI) m/z: 285.1 (M+H+).

Provenance & Evidence