[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[CH:12]=[N:11][NH:10][C:7]2=[N:8][CH:9]=1.[H][H].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O.O>[Br:3][C:4]1[CH:5]=[C:6]2[CH:12]=[N:11][N:10]([S:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:23])=[O:22])[C:7]2=[N:8][CH:9]=1
Sodium Hydride (0.667 g, 16.66 mmol) was added portion-wise over 15 mins to a stirred solution of 5-bromo-1H-pyrazolo[3,4-b]pyridine (3 g, 15.15 mmol, available from ChemGenx LLC) in N,N-dimethylformamide (30 ml) that had been cooled in an ice bath to 0° C. and placed under nitrogen. The mixture was stirred for 20 mins, until hydrogen evolution ceased, and then benzenesulfonyl chloride (2.148 ml, 16.66 mmol) was added. The mixture was stirred for 18 hours, letting the ice melt over this time. The solution was poured into stirring water (10 ml) and rapidly stirred for 15 mins. The mixture was then poured onto water (70 ml) and filtered. The orange solid obtained was dried in the vacuum oven for 18 h to afford the title compound (3.86 g).
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