[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[C:10]([NH2:13])[NH:11][N:12]=1.[Na].C([O:24][C:25](=O)[C:26]([CH3:29])=[CH:27]O)C.C(OCC)C>C(O)(=O)C>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([C:9]2[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])=[N:12][N:11]3[C:25]([OH:24])=[C:26]([CH3:29])[CH:27]=[N:13][C:10]=23)=[CH:19][CH:18]=1To a mixture of 5-(2-chlorophenyl)-4-(4-chlorophenyl)-2H-pyrazol-3-ylamine (I-3A-1b; 393 mg, 1.29 mmol) in acetic acid (4.3 ml) was added 3-hydroxy-2-methylacrylic acid ethyl ester sodium salt (590 mg, 3.88 mmol), portionwise. The reaction was heated at 100° C. for 2 hours (precipitate formed after 35 minutes). After cooling to room temperature, the precipitated solid was isolated by vacuum filtration and then repulped from diethyl ether to afford I-3A-1c as a colorless solid (141 mg, 30%): +ESI MS (M+1) 370.0; 1H NMR (400 MHz, DMSO-d6) δ 12.14 (br s, 1H), 7.75 (s, 1H), 7.50–7.38 (m, 4H), 7.32 (d, J=8.7 Hz, 2H), 7.17 (d, J=8.7 Hz, 2H), 2.01 (s, 3H).
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