Acetic Anhydride → 2-Acetamidopyridine-5-boronic acid pinacol ester

Participants

Reaction Steps

4-dimethylaminopyridine (17 mg, 0.139 mmol), triethylamine (0.19 mL, 1.36 mmol) and acetic anhydride (153 mg, 1.50 mmol) were added sequentially to a solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (300 mg, 1.36 mmol) in dichloromethane (15 mL). The reaction mixture was stirred at room temperature for 0.5 h, then diluted with 30 mL of dichloromethane, washed with 50 mL of a saturated aqueous solution of ammonium chloride. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated to give 225 mg of the product.

Provenance & Evidence