Benzyl azide → HCID 11165847, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of but-3-ynoic acid (2-benzoyl-4-chloro-phenyl)-amide (from Example 7) (0.056 g, 0.188 mmol) in 50% aq. tert-butanol (5 mL) was added benzyl azide (0.07 mL, 0.56 mmol), sodium ascorbate (0.012 g, 0.0564 mmol), and copper(II) sulfate pentahydrate (0.002 g, 5.64 μmol). After stirring at 70° C. for 15 hours, the reaction mixture was partitioned between ethyl acetate (15 mL) and water (15 mL). The aqueous layer was further extracted with ethyl acetate (2×15 mL) and the combined organic layers were dried (MgSO4) and concentrated. The residual yellow oil was purified by flash chromatography (silica gel) to afford 3-(1-benzyl-1H-[1,2,3]triazol-4-yl)-6-chloro-4-phenyl-1H-quinolin-2-one (0.064 g, 82% yield) as white solid. 1H NMR (300 MHz, CDCl3): δ 12.42 (s, 1H), 7.51 (s, 1H), 7.39-7.32 (m, 7.5H), 7.29 (s, 0.5H), 7.18-7.15 (m, 3H), 7.09-7.06 (m, 2H), 5.46 (s, 2H). MS: 413 (M+H).

Provenance & Evidence