Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:9][N:8](C3CCCCO3)[C:5]2=[CH:6][N:7]=1.[NH:23]1[CH:27]=[CH:26][N:25]=[CH:24]1.CNCCNC.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.[Cu]I>[N:23]1([C:2]2[CH:3]=[C:4]3[C:10]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)=[N:9][NH:8][C:5]3=[CH:6][N:7]=2)[CH:27]=[CH:26][N:25]=[CH:24]1A mixture of 100.0 mg (0.2791 mmol) of 5-bromo-3-phenyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine, 47.51 mg (0.6979 mmol) of 1H-Imidazole, 53.16 mg (0.2791 mmol) of Copper(I) iodide, 30.04 uL (0.2791 mmol) of N,N′-dimethylethylenediamine and 363.8 mg (1.116 mmol) of Cesium Carbonate in 3 ml of N,N-Dimethylformamide was heated at 120° C. for 48 hours. The mixture was filtered, the filtrate concentrated in high vacuum and the residue partitioned between ethyl acetate and water. The organic extracts were washed with water, brine, dried over MgSO4 and concentrated in vacuum. The residue was purified on 4 g of silica gel column, eluting 5-(1H-imidazol-1-yl)-3-phenyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine with a gradient of ethyl acetate in heptane. Yield 67 mg (69%). ESI MS m/z 346.1 (M+1).
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