Sodium Hydroxide → HCID 56773886, compound

Participants

Reaction Steps

A solution of 510 mg (2.96 mmol) of 6-methanesulfonylpyridin-3-ylamine in 1.25 mL of AcOH was added a solution of 0.15 mL (2.96 mmol) of bromine in 0.5 mL of AcOH at room temperature dropwise. The resulting slurry was stirred for 1 hour. The reaction was carefully basified to pH=10 with 6 M NaOH. The solution was then extracted with two 150 mL portions of dichloromethane, dried with magnesium sulfate, filtered, and concentrated in vacuo. The crude mixture showed a 3:1 mixture of product:dibromo product by NMR. These two products were separated by silica chromatography (hexanes/EtOAc) to afford 294 mg (40%) of 2-bromo-6-methanesulfonylpyridin-3-ylamine.

Provenance & Evidence