1,1'-Carbonyldiimidazole → 8-bromo-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Participants

Reaction Steps

To a solution of 1-4 (5.0 g, 26.6 mmol) in THF (50 mL) was added carbonyldiimidazole (5.61 g, 34.6 mmol), and the heterogeneous mixture was stirred for 2 h. The reaction was diluted with water (150 mL) and EtOAc (150 mL), causing a precipitate to form. The mixture was filtered through a sintered glass filter, yielding 2.0 g (35%) of 1-5 as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ12.73 (s, 1H), 7.88 (dd, J=7.2, 0.9 Hz, 1H), 7.58 (dd, J=7.2, 0.9 Hz, 1H), 6.51 (app t, J=7.2 Hz, 1H).

Provenance & Evidence