Pivaloyl chloride → N-(5-bromopyridin-2-yl)-2,2-dimethylpropanamide

Participants

Reaction Conditions

Reaction Steps

A solution of trimethylacetyl chloride (17.5 g, 146 mmol) in dichloromethane (25 ml) was added to a solution of 2-amino-5-bromopyridine (25.0 g, 144 mmol) in dichloromethane (100 ml) and triethylamine (24 ml) dropwise with stirring at 20° C. The reaction mixture was then stirred for 40 minutes, filtered, washed with water, dried and concentrated. Recrystallization from hexanes afforded 20.6 g (70%) of the title product as a white flaky solid. mp 63-64° C. 1H NMR (CDCl3): δ=8.82 (br, 1 H); 8.30 (d, 1 H); 8.19 (m, 2 H); 1.36 (s, 3 H). MS (El): m/z=256, 258 (M+, Br isotopes).

Provenance & Evidence