[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([NH:13][S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[C:11](C(O)=O)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.CCOC(C)=O.CCCCCC>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([NH:13][S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:11][CH:10]=[N:9]2)=[CH:6][CH:7]=1Dissolve 1-(4-Bromo-phenyl)-5-(propane-2-sulfonylamino)-1H-pyrazole-4-carboxylic acid (1.952 g, 5.03 mmol) in quinoline (2.79 mL) in a sealed tube. Add copper (0.16 g, 2.51 mmol) and immerse into a pre-heated (180° C.) oil bath and stir for 15 min. Cool to room temperature and remove the solvent under reduced pressure. Dilute with dichloromethane, wash with 1.0M HCl (2×50 mL), dry over sodium sulfate, filter, and concentrate to yield a residue. Subject to silica gel flash column chromatography (15-55% EtOAc/n-hexane) to yield the title compound (1.323 g, 76%).
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