Sodium periodate → 3-Benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazine-2-carbaldehyde

Participants

Reaction Steps

Sodium periodate (17.3 g, 80.7 mmol) was added to a pH 7.0 buffered solution (75 mL) of 3-benzyl-5-chloro-2-(2-dimethylamino-vinyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (5.3 g, 16.1 mmol) in THF (150 mL) at room temperature. The reaction mixture was stirred at room temperature for 1.5 h. The reaction mixture was filtered through Celite® and the solids washed with CHCl3 (100 ml). The filtrate was wash with saturated NaCl (2×50 mL), dried (Na2SO4), filtered and concentrated in vacuo. The solid was azeotroped with toluene (2×50 mL) to afford the title compound as a solid (4.6 g, 100%): TLC, Rf=0.5 (2/1 hexane/EtOAc, UV); 1H NMR (CDCl3) δ 9.34 (s, 1H), 7.33 (m, 1H), 7.16–7.27 (m, 5H), 6.60 (m, 1H), 5.62 (s, 2H).

Provenance & Evidence