[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.Cl.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][NH2:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][N:19]([C:16]1[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=1)[NH2:20]To a suspension of 2-bromobenzyl bromide (500 mg, 2.00 mmol) and 4-methoxyphenylhydrazine hydrochloride (348 mg, 2.00 mmol) in N,N-dimethylformamide (8 mL) was added potassium carbonate (1.38 g, 10.0 mmol). The reaction mixture was heated at 90° C. for 4 hours. The reaction was partitioned between water and methylene chloride. The methylene chloride was dried (MgSO4), concentrated and purified by SiO2 chromatography with 10-50% ethyl acetate/hexanes to give 298 mg of the title compound. LC-MS (C14H18BrN2O calculated 306) m/z 307 (M+H).
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