N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)propionamide → N-(4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)propionamide

Participants

Reaction Steps

A solution of N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)propionamide (0.42 g, 1.389 mmol) in 2:1 EtOAc/MeOH (30 mL) was treated with palladium on carbon (50% wet, 0.165 g, 0.139 mmol) and hydrogenated (1 atm) for 2 days. The solids were removed via filtration through diatomaceous earth, washed well with MeOH and the filtrate was concentrated to dryness to afford N-(4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)propionamide (320 mg, 85%). 1H NMR (400 MHz, DMSO-d6): δ 10.41 (s, 1H), 8.12 (d, J=5.7 Hz, 1H), 7.56 (d, J=2.4 Hz, 1H), 7.15 (d, J=8.7 Hz, 1H), 6.56 (dd, J=5.7, 2.4 Hz, 1H), 6.34 (d, J=8.7 Hz, 1H), 5.93 (s, 2H), 2.33 (q, J=7.5 Hz, 2H), 2.04 (s, 3H), 1.00 (t, J=7.5 Hz, 3H); MS (ESI) m/z: 273.2 (M+H+).

Provenance & Evidence