[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2.[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.O>[C:16]1([S:22]([N:11]2[C:12]3[C:8](=[C:7]([C:2]4[CH:3]=[N:4][CH:5]=[CH:6][N:1]=4)[CH:15]=[CH:14][CH:13]=3)[CH:9]=[CH:10]2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=14-Pyrazin-2-yl-1H-indole (0.060 g, 0.307 mmol, Intermediate 65), benzensulfonyl chloride (0.071 g, 0.40 mmol) and tetrabutylammonium hydrogen sulfate (0.010 g, 0.031 mmol) were dissolved in dichloromethane (3 mL) and NaOH (0.061 g, 1.5 mmol) in water (1 mL) was added. The mixture was stirred at rt overnight and the mixture was diluted with dichloromethane and water and extracted with dichloromethane (2×). The organic phase was dried (MgSO4) and evaporated. The crude product was purified by flash chromatography using CH2Cl2 to 1% MeOH in CH2Cl2 as the eluent. Yield: 81 mg (79%). White solid. MS (electronspray; [M+H]+) m/z 336.4.
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