[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][NH:10][C:4]=2[CH:3]=1.Br[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[N:13]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.[Cu](I)I>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[N:13]=3)[C:4]=2[CH:3]=1A mixture of 6-chloro-1H-pyrazolo[4,3-c]pyridine (13.778 mmol, 2115.9 mg), 2-bromo-6-fluoro-pyridine (15.156 mmol, 2667.3 mg), N,N′-Dimethylethylenediamine (13.778 mmol; 1.215 g; 1.37 mL), Copper iodide (13.778 mmol; 2650.5 mg), and potassium carbonate (15.156 mmol; 2.12 g) in 1,4-Dioxane (10 mL) was purged with Argon, then sealed and stirred at 100° C. for 20 hours. The mixture was cooled to room temperature, and then filtered through Celite. The filtrate was concentrated; the residue was purified on silica and eluted with 0 to 100% Ethyl acetate in Heptane to give 6-Chloro-1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridine as an off-white solid (1.90 g, 55%) MS (ESI) m/z: 249 [M+H]+
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