Triethylamine → N-(5-bromopyridin-2-yl)-2,2-dimethylpropanamide

Participants

Reaction Steps

A solution of 5.00 g (28.9 mmol) of 2-amino-5-bromopyridine in 20 mL of dichloromethane was treated sequentially with 3.50 g (34.6 mmol) of triethylamine followed by 3.50 g (29.2 mmol) of trimethylacetyl chloride. The reaction mixture was filtered after about 1 hour, and the filtrate was evaporated to a colorless oil. This was crystallized from hexanes, filtered and washed to afford 3.36 g of N-(5-bromo-pyridin-2-yl)-2,2-dimethyl-propionamide as white crystals, mp 57-59° C. 1H NMR (deuterochloroform) δ=8.28 (d, 1 H); 8.16 (d, 1 H); 7.96 (br, 1 H); 7.75 (d of d, 1 H); 1.29 (s, 9 H): MS (NH3CL): m/z=257,259 (M+H+, Br isotopes).

Provenance & Evidence