[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][CH:5]=1.[NH:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH2:17][N:18]([CH3:20])[CH3:19].C([O-])([O-])=O.[K+].[K+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>CS(C)=O.[Cu]I.CO.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[CH2:17][N:18]([CH3:20])[CH3:19])=[CH:6][CH:5]=1
Part G. 4-Iodo-benzoic acid methyl ester (1.42 g, mmol) and (1H-imidazol-2-ylmethyl)-dimethyl-amine (0.68 g, mmol) were stirred in DMSO (3.5 mL) under N2. K2CO3 (1.52 g, mmol) was added followed by the addition of CuI (0.52 g, mmol) and 1,10-phenanthroline (0.46 g, mmol). The reaction mixture was heated at 120–125° C. for 2 h. After cooling, EtOAc was added. It was washed with dil. NH3H2O, H2O, brine, dried over MgSO4, filtered, and concentrated to dryness. The residue was purified by FCC (silica gel, CH2Cl2:EtOAc=1:0 to 0:1, then 10% MeOH) to give pure 4-(2-dimethylaminomethyl-imidazol-1-yl)-benzoic acid methyl ester (0.56 g, yield 40%). 1H NMR (CDCl3) δ 7.84 (d, J=8.4 Hz, 2H), 7.40 (d, J=8.4 Hz, 2H), 6.87 (d, J=0.9 Hz, 1H), 6.80 (d, J=0.9 Hz, 1H), 3.65 (s, 3H), 3.10 (s, 2H), 1.96 (s, 6H) ppm.
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