Pivaloyl chloride → N-(6-Bromopyridin-2-yl)-2,2-dimethylpropanamide

Participants

Reaction Steps

To a solution of 6-bromopyridin-2-amine (10 g, 57.79 mmol, 1 eq.) in 150 ml of DCM were added TEA (17.54 g, 173.3 mmol, 3 eq.) and 2,2-dimethylpropionyl chloride (10.45 g, 86.69 mmol, 1.5 eq.) dropwise. The temperature rose slowly. The reaction was stirred overnight at r.t. The white solid was removed by filtration and the solvent was evaporated. The crude was dissolved in with EtOAc and washed with 0.1N aq. HCl, sat. aqueous NaHCO3. The organics were dried over MgSO4 and concentrated. The resulting solid was recrystallized in EtOAc to give N-(6-bromopyridin-2-yl)-2,2-dimethylpropanamide (13.52 g, 91% yield) as a white solid.

Provenance & Evidence