[Cl:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=[O:8].[N:11]1[N:12]=[CH:13][NH:14][CH:15]=1.C([O-])([O-])=O.[Cs+].[Cs+].CS(C)=O>CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[C:6]([CH:9]=1)[CH:7]=[O:8]To a reaction vessel was added 5-chloro-2-fluorobenzaldehyde (1.29 g, 7.89 mmol), 4H-1,2,4-triazole (0.574 g, 7.89 mmol), Cs2CO3 (2.83 g, 8.68 mmol) and DMSO (15.78 ml). The mixture was capped and heated at 45° C. for 4 hrs before cooling down to rt and stirred at rt over weekend. The reaction mixture was diluted with EtOAc, washed with water and brine, dried over MgSO4, filtered, concentrated and purified by flash chromatography to yield 71A as white solid product (674 mg, 41%). 1H NMR (500 MHz, DMSO-d6) δ 9.90 (s, 1H), 9.17 (s, 1H), 8.33 (s, 1H), 7.99-7.91 (m, 2H), 7.84 (d, J=8.5 Hz, 1H).
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