[N+:1]([C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]([CH:20]3[CH2:22][CH2:21]3)=[O:19])[CH:12]=2)=[CH:6][CH:5]=1)([O-])=O.O.NN>CO.[Ni]>[NH2:1][C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]([CH:20]3[CH2:21][CH2:22]3)=[O:19])[CH:12]=2)=[CH:6][CH:5]=1A solution of N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide (1.50 g, 5.00 mmol) in MeOH (30 mL) was treated with hydrazine hydrate (1.50 g, 30.0 mmol) followed by Raney nickel (0.300 g, 5.11 mmol) and stirred at RT for 3 h. The solids were removed via filtration through diatomaceous earth, rinsed with DCM, then MeOH and the filtrate concentrated to dryness to afford N-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide (1.17 g, 87%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.21 (s, 1H), 8.56 (d, J=5.7 Hz, 1H), 8.19 (s, 1H), 8.01 (s, 1H), 7.68 (d, J=8.9 Hz, 1H), 7.06 (m, 1H), 6.92 (d, J=8.9 Hz, 1H), 6.43 (s, 2H), 2.37 (m, 1H), 1.18 (s, 4H); MS (ESI) m/z: 271.2 (M+H+).
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