[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.C([N-]C(C)C)(C)C.[Li+].[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])(O)=O.[Na+]>O1CCCC1.C1COCC1.CCCCCCC>[C:18]1([S:24]([N:1]2[C:5]3=[CH:6][N:7]=[CH:8][CH:9]=[C:4]3[CH:3]=[CH:2]2)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1To a suspension of 1H-pyrrolo[2,3-c]pyridine (700 mg, 5.9 mmol) in tetrahydrofuran (14.0 mL) was added lithium diisopropylamide (2.9 mL of a 2 M solution in THF/heptane, 5.9 mmol) at −78° C. After 0.5 h, benzenesulfonyl chloride (0.79 mL, 6.2 mmol) was added dropwise. The mixture was allowed to slowly warm to ambient temperature overnight. The reaction mixture was poured into 2% aq NaHCO3 (30 mL) and extracted with EtOAc (2×25 mL). The combined extracts were washed with H2O (20 mL) and saturated NaCl (20 mL), dried (Na2SO4) and concentrated under reduced pressure. Purification by column chromatography (silica gel, 1:1 hexanes/EtOAc) gave 1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridine (1.2 g, 80%): 1H NMR (500 MHz, DMSO-d6) δ 6.94 (1H, d, J=6.0 Hz), 7.59-7.66 (3H, m), 7.70-7.75 (1H, m), 8.07-8.10 (3H, m), 8.38 (1H, d, J=8.8 Hz), 9.23 (1H, s); ESI MS m/z 259 [C13H10N2O2S+H]+.
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