Ethylenediamine → HCID 178470161, compound

Participants

Reaction Conditions

Reaction Steps

A degassed mixture of ethyl 3-hydroxy-6-iodoquinoxaline-2-carboxylate (351 mg, 1.0 mmol), sodium methanesulfinate (132 mg, 1.3 mmol), copper(I) triflate benzene complex (25 mg, 5 mol %) and ethylenediamine (0.01 mL, 10 mol %) in anhydrous DMSO (1.0 mL) was heated at 110° C. in a sealed reaction vessel for 20 h. The cooled mixture was diluted with ethyl acetate (10 mL) and filtered through a plug of silica gel under reduced pressure, eluting with additional ethyl acetate (50 mL). The filtrate was washed with water (20 mL) and brine (20 mL), dried over sodium sulfate and filtered. The solvents were removed under reduced pressure and the residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate, to provide ethyl 3-hydroxy-6-(methylsulfonyl)quinoxaline-2-carboxylate as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 11.61 (br S, 1H), 8.16 (d, J=8.9 Hz, 1H), 8.01 (s, 1H), 7.91 (d, J=9.9 Hz, 1H), 4.58 (q, J=6.7 Hz, 2H), 3.16 (s, 3H), 1.49 (t, J=6.7 Hz) ppm; ESI MS m/z 297 [M+H]−.

Provenance & Evidence