4-acetyl-N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamide → N-(5-Bromo-2-chloro-3-pyridinyl)-4-(1-hydroxy-1-methylethyl)benzenesulfonamide

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Reaction Steps

4-acetyl-N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamide (123.5 mg, 0.317 mmol) was dissolved in THF (2.6 ml) and cooled in an ice water bath under nitrogen. Then, methylmagnesium bromide (0.65 ml, 1.4 M solution in toluene/tetrahydrofuran (75:25), 0.91 mmol) was added via syringe, and the reaction was allowed to slowly warm to room temperature. After 2 hours and 45 minutes, more methylmagnesium bromide (0.50 ml) was added, and stirring was continued at room temperature. After 75 minutes, more methylmagnesium bromide (0.93 ml) was added, and stirring was continued. After another hour, the reaction quenched with saturated ammonium chloride. The layers were separated, and the aqueous phase was extracted with 10:1 DCM/MeOH. Organic extracts combined, concentrated, and taken on to the next step. MS (ESI pos. ion) m/z: 405 (MH+, 79Br), 407 (MH+, 81Br). Calculated exact mass for C14H14BrClN2O3S 404 (79Br), 406 (81Br).

Provenance & Evidence