[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:15]=[N:16][C:17]([N+:20]([O-])=O)=[CH:18][CH:19]=3)[CH:10]=[CH:9][N:8]=2)=[CH:5][N:6]=1.[NH4+].[Cl-]>CO.C1COCC1.CCOC(C)=O.[Zn]>[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[N:16][CH:15]=3)[CH:10]=[CH:9][N:8]=2)=[CH:5][N:6]=1A 0° C. mixture of 2-methyl-5-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)oxazole (323 mg, 1.083 mmol) and NH4Cl (2.317 g, 43.3 mmol) in MeOH (8 mL) and THF (8 mL) was treated portion-wise with zinc dust (708 mg, 10.83 mmol), allowed to warm to RT and stirred overnight. The mixture was diluted with EtOAc, warmed slightly, the solids removed via filtration through diatomaceous earth and washed with EtOAc. The filtrate was concentrated to dryness, treated with EtOAc, heated to reflux, the solids removed via hot filtration and the filtrate concentrated to dryness to afford 5-((2-(2-methyloxazol-5-yl)pyridin-4-yl)oxy)pyridin-2-amine (324 mg, 112%). 1H NMR (400 MHz, DMSO-d6): δ 8.43 (d, J=5.7 Hz, 1 H), 7.83 (d, J=2.9 Hz, 1 H), 7.60 (s, 1 H), 7.31 (dd, J=8.9, 3.0 Hz, 1 H), 7.06 (d, J=2.5 Hz, 1 H), 6.83 (dd, J=5.7, 2.5 Hz, 1 H), 6.53 (d, J=8.9 Hz, 1 H), 6.07 (s, 2 H), 2.46 (s, 3 H); MS (ESI) m/z: 269.1 (M+H+).
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