[H-].[Na+].[Cl:3][C:4]1[C:5]([Cl:13])=[C:6]2[CH:12]=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.O>CN(C)C=O>[Cl:13][C:5]1[C:4]([Cl:3])=[CH:9][N:8]=[C:7]2[N:10]([S:20]([C:17]3[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=3)(=[O:22])=[O:21])[CH:11]=[CH:12][C:6]=12To a cold (0° C.) suspension of sodium hydride (60% dispersion in mineral oil, 0.556 g, 13.9 mmol) in N,N-dimethylformamide (20 mL) was added a solution of the 5-chloro-4-chloro-1H-pyrrolo[2,3-b]pyridine (2 g, 10.69 mmol) in N,N-dimethylformamide (10 mL) slowly over 5 minutes. The reaction was allowed to stir at ambient temperature for 0.5 hours, and was again cooled to 0° C. A solution of para-toluenesulfonyl chloride (2.14 g, 11.23 mmol) in N,N-dimethylformamide (5 mL) was added, and the reaction was stirred at ambient temperature for 1.5 hours. The reaction was poured into 60 mL water cooled in an ice bath. The suspension was filtered. The solid was collected and purified by flash chromatography on a silica gel, eluting with a gradient of 30% to 100% dichloromethane in hexane, to provide the title compound. MS ESI(+) m/z 340.8 [M+H]+.
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