Pyridine → N-(5-Bromo-2-chloropyridin-3-yl)benzenesulfonamide

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Reaction Steps

A solution of benzenesulfonyl chloride (1.23 mL, 9.62 mmol, 2 eq) in DCM (50 mL) is added dropwise over 15 min to a solution of 3-amino-5-bromo-2-chloropyridine [Jouve, K.; Bergman, J., Journal of Heterocyclic Chemistry, (2003), 40(2), 261-268] (1 g, 4.81 mmol) and pyridine (1.94 ml, 24 mmol, 5 eq) in DCM (20 mL), under an argon atmosphere. The resulting mixture is stirred for 20 h at rt, concentrated, diluted with H2O and extracted with DCM. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (DCM) to afford 163 mg of the title compound as a white solid: ESI-MS: 346.9 [M−H]−; tR=4.33 min (System 1); TLC: Rf=0.23 (DCM).

Provenance & Evidence