C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Br:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][S:19]([CH3:22])(=[O:21])=[O:20])=[N:16][CH:17]=1.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:33])(=O)=O)=CC=1>O1CCCC1>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([CH:18]([F:33])[S:19]([CH3:22])(=[O:21])=[O:20])=[N:16][CH:17]=1Lithium bis(trimethylsilyl)amide (0.45 mL, 1M in tetrahydrofuran, 0.45 mmol) is added to a solution of commercially available 5-bromo-2-(methylsulfonylmethyl)pyridine (102 mg, 0.408 mmol) in tetrahydrofuran (5 mL) at −78° C. After 45 minutes N-Fluorodibenzenesulfonamide (156 mg) in tetrahydrofuran (10 mL) is added to the reaction mixture at −78° C. over 5 minutes. After stirring for 20 minutes the reaction is quenched with water (10 mL) and ethyl acetate(10 mL). The reaction mixture is partitioned between saturated aqueous ammonium chloride solution (10 mL) and ethyl acetate (10 mL). The combined organic layers are washed with brine and concentrated to give the crude product, which is purified by flash column chromatography eluting from neat hexane to neat ethyl acetate to give the title compound (50 mg): m/z (Cl) 268 (M+H).
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