N-bromobutanimide → HCID 10237594, compound

Participants

Reaction Conditions

Reaction Steps

N-Bromosuccinimide (2.77 g) was added to a solution of N-(4-chlorobenzyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide (Example 78, 2.46 g) in CHCl3 (100 mL). The reaction mixture was heated to 50° C. for 18 h. The mixture was allowed to cool to room temperature and was washed with water (100 mL) and brine (100 mL). The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. The resulting solid was purified by column chromatography (CH2Cl2/methanol, 99/1) followed by recrystallization from ethyl acetate to yield 1.87 g (61%) of the title compound as a white solid. Physical characteristics. M.p. 232-233° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.50, 8.57, 7.41-7.32, 7.23, 4.55, 3.92; MS (EI) m/z 394 (M+), 396 (M++2).

Provenance & Evidence