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

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A solution of N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide (0.44 g, 1.526 mmol) in MeOH (30 mL) was treated with palladium on carbon (50% wet, 0.162 g, 0.153 mmol) and hydrogenated (1 atm) at RT for 24 h. The solids were removed via filtration through diatomaceous earth, washed well with MeOH and the filtrate concentrated to afford N-(4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)acetamide (370 mg, 94%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.46 (s, 1 H), 8.10 (d, J=5.7 Hz, 1 H), 7.53 (d, J=2.3 Hz, 1 H), 7.13 (d, J=8.7 Hz, 1 H), 6.53 (dd, J=5.7, 2.4 Hz, 1 H), 6.32 (d, J=8.7 Hz, 1 H), 5.91 (s, 2 H), 2.02 (s, 3 H), 2.01 (s, 3 H); MS (ESI) m/z: 259.2 (M+H+).

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