[Br:1][C:2]1[C:6]2=[N:7][CH:8]=[CH:9][N:10]=[C:5]2[NH:4][CH:3]=1.[H-].[Na+].[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O>[Br:1][C:2]1([S:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:21])=[O:20])[C:6]2=[N:7][CH:8]=[CH:9][N:10]=[C:5]2[NH:4][CH2:3]1A solution of 7-bromo-5H-pyrrolo[3,2-b]pyrazine (1 g, 5.05 mmol) in N,N-dimethylformamide (10 ml) was cooled at 0° C., and sodium hydride (167 mg, 5.55 mmol) was added in several portions. After stirring at 0° C. for 30 minutes, benzenesulfonyl chloride (980 mg, 5.55 mmol) was added via syringe. The mixture was allowed to warm up to room temperature and stirred for 4 hours. The reaction mixture was partitioned between ethyl acetate and brine. The organic phase was washed with brine and concentrated. The residue was purified by flash chromatography (30% ethyl acetate in hexane) to afford the title compound. MS (DCI/NH3) m/z 339 (M+H)+.
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