I[C:2]1[CH:3]=[N:4][N:5]([CH3:10])[C:6]=1[C:7](O)=[O:8].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1.[CH2:19](OCC)[CH3:20].[OH-].[Na+]>C(=O)([O-])[O-].[Na+].[Na+].[Cu]>[CH2:19]([N:11]1[C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=2[C:7](=[O:8])[C:6]2[N:5]([CH3:10])[N:4]=[CH:3][C:2]1=2)[CH3:20]
A mixture of 4-iodo-1-methyl-1H-pyrazole-5-carboxylic acid ((Y. A. Manaev et al., J. Gen. Chem. USSR. (Engl. Transl.), 1982, 52, 2291), 2.92 g, 11.6 mmol), p-toluidine (6.20 g, 57.9 mmol), and copper powder (1.17 g, 18.4 mmol) in 5% aqueous sodium carbonate (60 ml) was stirring at 100° C. for 5 h. After cooling to room temperature, diethyl ether (100 ml) and 2N aqueous sodium hydroxide (100 ml) were added. This mixture was filtered through a pad of Celite, which was washed with 2N sodium hydroxide (200 ml) and ether (100 ml). The separated aqueous layer was washed with ether (100 ml), filtered through a pad of Celite again, and acidified with concentrated hydrochloric acid. The precipitate was collected by filtration, and washed with water to give 1.77 g (76.6 mmol, 66%) of the title compound as a gray powder.
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