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

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Reaction Steps

A solution of N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide (0.50 g, 1.591 mmol) in 2:1 EtOAc/MeOH (30 mL) was treated with palladium on carbon (50% wet, 0.188 g, 0.159 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)cyclopropanecarboxamide (400 mg, 88%). 1H NMR (400 MHz, DMSO-d6): δ 10.77 (s, 1H), 8.13 (d, J=5.7 Hz, 1H), 7.52 (d, J=2.4 Hz, 1H), 7.14 (d, J=8.7 Hz, 1H), 6.58 (dd, J=5.7, 2.4 Hz, 1H), 6.32 (d, J=8.7 Hz, 1H), 5.92 (s, 2H), 2.03 (s, 3H), 1.95 (m, 1H), 0.76 (s, 4H); MS (ESI) m/z: 285.1 (M+H+).

Provenance & Evidence