[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[N:17]=[CH:16][NH:15][N:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)#[CH:19].[OH-].[Na+].C(OCC)(=O)C.CCCCCC>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[N:17]=[CH:16][N:15](/[CH:19]=[CH:18]\[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[N:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1In a 25 mL, 3 Neck round-bottomed flask equipped with nitrogen inlet and a rubber septum, 3-(3-methoxy-5-(trifluoromethyl)phenyl)-1H-1,2,4-triazole (0.25 g, 1.0 eq.), 2-ethynylpyridine (0.1 ml, 1.0 eq.) and sodium hydroxide (0.1028 g, 2.5 eq.) were dissolved in DMF (5.0 mL). The reaction mixture was stirred at 75-80° C. The progress of the reaction was followed by TLC analysis on silica gel with 50% ethyl acetate-hexane as mobile phase which shows that starting material was consumed after 15 h. Reaction mixture was diluted by water and extracted with ethyl acetate, combined organic layer was dried over sodium sulphate and distilled under reduce pressure (25° C., 20 mmHg) to obtain crude material. The crude compound was purified by column chromatography using 60/120 silica gel and ethyl acetate in hexane as mobile phase. The column was packed in Hexane and started eluting in ethyl acetate in gradient manner starting with fraction collection. The compound started eluting from 18% ethyl acetate in hexane. Fractions containing such TLC profile were collected together to obtain pure compound 0.005 g; LCMS (%): Retention time 3.476 min (97.44%); (Z)-2-(2-(3-(3-methoxy-5-(trifluoromethyl)phenyl)-1H-1H-1,2,4-triazole-1-yl)vinyl)pyridine: 1H NMR (400 MHz, DMSO) δ: 9.61 (s, 1H), 8.67-8.68 (d, 1H, J=4.8 Hz), 8.03 (S 1H), 7.86 (s, 1H), 7.71-7.76 (doublet of triplet, 1H), 7.30-7.732 (d, 1H, J=8 Hz), 7.20 (s, 1H), 7.14-7.16 (d, 1H, J=10.4 Hz), 6.40-6.42 (d, 1H, J=10.8 Hz), 3.94 (s, 1H). LCMS for C17H13F3N4O [M+H]+ 1345.3 found at 346.8 at 3.476 min (LCMS: 97.44%).
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