[CH2:1]([C:4]1[C:5]([Cl:13])=[C:6]2[CH:12]=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1)[CH:2]=[CH2:3].[H-].[Na+].[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17]>CN(C=O)C>[CH2:1]([C:4]1[C:5]([Cl:13])=[C:6]2[CH:12]=[CH:11][N:10]([S:16]([C:19]3[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[C:7]2=[N:8][CH:9]=1)[CH:2]=[CH2:3]5-Allyl-4-chloro-1H-pyrrolo[2,3-b]pyridine (2.24 g, 11.6 mmol) in DMF (25 mL) was cooled to about 0° C. then treated with 60 wt % NaH (0.558 g, 13.9 mmol). The mixture was stirred for about 30 min then TsCl (2.44 g, 12.8 mmol) was added. The mixture was stirred for about 15 min at about 0° C. then warmed to rt for about 30 min. The solvents were evaporated under reduced pressure then the residue was stirred with DCM (40 mL) and saturated aqueous NaHCO3 (35 mL) for about 15 min. The layers were separated then the aqueous layer was extracted with DCM (20 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated in vacuo to give 5-allyl-4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine (4.0 g, 111%, crude): LC/MS (Table 2, Method a) Rt=3.18 min; MS m/z 347 (M+H)+.
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