Br[C:2]1[N:3]=[CH:4][N:5]([CH3:14])[C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[C:15]([Cu])#[N:16]>CN(C=O)C.N1C=CC=CC=1>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]2[N:5]([CH3:14])[CH:4]=[N:3][C:2]=2[C:15]#[N:16])=[CH:8][CH:9]=1To 4-bromo-5-(4-chlorophenyl)-1-methyl-1H-imidazole (1.3 g, 4.79 mmol) in DMF (8.4 mL) and pyridine (1.6 mL) was added CuCN (1.3 g, 14.4 mmol). The reaction was heated in a microwave reactor at 200° C. for 35 min. After cooling to ambient temperature, the reaction was quenched by addition of a 3:1 solution of NH4OH/saturated aqueous NH4Cl (60 mL). The reaction was extracted with EtOAc, organics separated, washed with saturated aqueous NaHCO3, and dried with saturated aqueous NaCl. Solvents were removed in vacuo and the residue purified by column chromatography on silica to provide desired product and recovered starting material. The recovered starting material was resubjected to the reaction conditions and purified as above to provide additional desired product. MS (m/z) 218.3 [M+H]+.
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