C(=O)([O-])[O-].[K+].[K+].[C:7]([C:9]1[CH:10]=[C:11]([S:16]([N:19]([C:27]2[N:28]=[CH:29][S:30][CH:31]=2)[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:18])=[O:17])[CH:12]=[CH:13][C:14]=1F)#[N:8].[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[C:35]([I:40])[CH:34]=1>CN(C)C=O.C(OCC)(=O)C>[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][C:14]2[CH:13]=[CH:12][C:11]([S:16]([N:19]([C:27]3[N:28]=[CH:29][S:30][CH:31]=3)[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:18])=[O:17])=[CH:10][C:9]=2[C:7]#[N:8])=[C:35]([I:40])[CH:34]=1To a suspension of potassium carbonate (0.0549 g, 0.000397 mol) in N,N-dimethylformamide (3.0 mL) was added tert-butyl [(3-cyano-4-fluorophenyl)sulfonyl]1,3-thiazol-4-ylcarbamate (Preparation 250, 0.1004 g, 0.000167 mol) and stirred at room temperature under nitrogen for 10 minutes. 4-chloro-2-iodophenol (0.067 g, 0.000263 mol) was added and stirred at room temperature for 16 hours. The reaction was diluted with ethyl acetate (10.0 mL). The organic phase was washed saturated aqueous sodium chloride solution (2×10.0 mL), dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a yellow oil, 162 mg, 100% yield.
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