Sodium Thiosulfate → 4-chloro-N-[2-(2-chloro-5-nitro-benzoyl)-5-methyl-pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide

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To a solution of 4-chloro-N-{2-[(2-chloro-5-nitro-phenyl)-hydroxy-methyl]-5-methyl-pyridin-3-yl}-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (441 mg, 0.76 mmol) in CH2Cl2 (5 mL) was added Dess-Martin periodinane (645 mg, 1.52 mmol) and stirred for 6 h at room temperature. 10% Na2S2O3 (5 mL) and saturated aqueous NaHCO3 solution (5 mL) was added and stirred for 30 min. Aqueous layer was separated and extracted with EtOAc (2 ×25 mL). Combined organic layers were washed with saturated aqueous NaHCO3 solution (20 mL), brine (20 mL), dried (anhydrous Na2SO4), concentrated and purified (SiO2, 40% EtOAc-hexanes) to obtain 4-chloro-N-[2-(2-chloro-5-nitro-benzoyl)-5-methyl-pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (230 mg) as yellow syrup in 52% yield. ESMS m/z (relative intensity): 545.9 (M-31)+(100), 578 (M+H)+(50), 599.9 (M+Na)+(65).

Provenance & Evidence