[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:4][N:3]=1.Cl[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=2)[N:3]=1
A mixture of 3-methyl-5-phenyl-1H-pyrazole (760 mg, 5.0 mmol), [4-(chloromethyl)phenyl]methanol (850 mg, 5.43 mmol), potassium carbonate (1.38 g, 10.0 mmol) and N,N-dimethylformamide (20 mL) was stirred at 120° C. for 1 hr. The reaction mixture was poured into 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried using a Presep Dehydration tube (manufactured by Wako Pure Chemical Industries, Ltd.) and concentrated. The residue was purified by silica gel column chromatography (10%-80% ethyl acetate/hexane) to give the title compound (850 mg, yield 61%) as colorless crystals. 1H NMR (CDCl3) δ: 2.21 (3H, s), 4.66 (2H, s), 5.33 (2H, s), 6.38 (1H, s), 7.13 (2H, d, J=8.1 Hz), 7.27-7.34 (3H, m), 7.34-7.42 (2H, m), 7.77-7.83 (2H, m).
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