[NH2:1][C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([OH:12])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[Cl:19][C:20]1[CH:25]=[C:24](Cl)[CH:23]=[CH:22][N:21]=1>CC(N(C)C)=O>[Cl:19][C:20]1[CH:25]=[C:24]([O:12][C:5]2[CH:4]=[CH:3][C:2]([NH2:1])=[N:7][C:6]=2[C:8]([F:11])([F:9])[F:10])[CH:23]=[CH:22][N:21]=1A solution of 6-amino-2-(trifluoromethyl)pyridin-3-ol (0.092 g, 0.517 mmol) in DMA (5 mL) was sparged with Ar, treated with potassium t-butoxide (0.087 g, 0.775 mmol), stirred for 1 minute, treated with 2,4-dichloropyridine (0.092 g, 0.620 mmol), flushed with Ar and heated at 95° C. overnight. The mixture was cooled to RT, treated with EtOAc, washed with satd. NaHCO3 (2×), dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 5-((2-chloropyridin-4-yl)oxy)-6-(trifluoromethyl)pyridin-2-amine (62 mg, 41%). 1H NMR (400 MHz, DMSO-d6): δ 8.27-8.24 (m, 1H), 7.52-7.49 (m, 1H), 7.04 (s, 1H), 6.94-6.91 (m, 1H), 6.76 (d, J=9.1 Hz, 1H), 6.66 (s, 2H); MS (ESI) m/z: 290.1 (M+H+).
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