Bromoacetyl bromide → 2-bromo-N-isopropyl-N-(6-methoxy-pyridin-3-yl)-acetamide

Participants

Reaction Steps

To a solution of isopropyl-(6-methoxy-pyridin-3-yl)-amine (6.73 g, 41.0 mmol) in CH2Cl2 (130 mL) at 0° C. was added diisopropylethylamine (7.15 mL, 41.0 mmol) followed by bromoacetyl bromide (8.28 g, 41.0 mmol) in CH2Cl2 (60 mL) over 0.5 hours. The reaction was stirred at room temperature for 24 hours and was diluted with water. The organic solution was washed with brine (1×), dried (MgSO4), filtered and concentrated. The residue was purified by medium pressure chromatography eluting with a solvent gradient (1% MeOH in CH2Cl2 to 5% MeOH in CH2Cl2) to provide 2.27 g of 2-bromo-N-isopropyl-N-(6-methoxy-pyridin-3-yl)-acetamide. 1H NMR (CD3OD) δ 8.08 (d, 1H), 7.62 (dd, 1H), 6.89 (d, 1H), 4.84 (m, 1H), 3.9 (s, 3H), 3.60 (s, 2H), 1.06 (m, 6H).

Provenance & Evidence