Water → HCID 22614889, compound

Participants

Reaction Steps

Diisobutylaluminium hydride (1M in tetrahydrofuran, 2.5 mL, 2.5 mmol) was added to a solution of 6,7-dichloro-2,3-dimethoxy-5-(3-ethoxycarbonyl-5-phenyl-4H-1,2,4-triazol-4-yl)quinoxaline (Preparation 93, 237 mg, 0.5 mmol) in dichloromethane (10 mL) at room temperature under nitrogen. After 1 hour, a further portion of diisobutylaluminium hydride (1M in tetrahydrofuran, 1 mL, 1 mmol) was added, the mixture was stirred for a further 1 hour, then saturated aqueous ammonium chloride solution (10 mL) was added. Dichloromethane (50 mL) and water (50 mL) were added and the mixture was filtered through ARBOCEL (trade mark), washing the residue with warm dichloromethane:methanol (9:1, by volume, 100 mL). The organic layer was separated, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel, by gradient elution using hexane:ethyl acetate:methanol (1:1:0 changing to 0:1:0 changing to 0:95:5, by volume) to give the title compound (70 mg, 79%) as an off-white solid.

Provenance & Evidence