[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1I)[CH:11]=[O:12].C(=O)([O-])[O-].[Cs+].[Cs+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I.CN(C=O)C>[CH:4]1[N:3]2[C:2]([CH2:6][O:7][C:8]3[CH:9]=[C:10]([CH:11]=[O:12])[CH:13]=[CH:14][C:15]=32)=[N:1][CH:5]=1To a vial, were added copper(I) iodide (27.8 mg, 0.146 mmol), 3-(1H-imidazol-2-ylmethoxy)-4-iodobenzaldehyde (127.7 mg, 0.389 mmol), cesium carbonate (267 mg, 0.819 mmol) and a stir bar. The reaction vial was purged with Argon 3 times. The (R,R)-(−)-N,N′-dimethyl-1,2-cyclohexanediamine (50 mg, 0.352 mmol) and DMF (2 ml) were added. The mixture was heated at 110° C. for 1 h. LCMS showed product formation. The mixture was filtered and purified on reverse phase HPLC to afford desired product (24.8 mg, 0.124 mmol, 31.8% yield).
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