3-Butenoic acid → HCID 46916454, compound

Participants

Reaction Steps

To a solution of vinylacetic acid (43 μL, 0.497 mmol) and oxalyl chloride (48 μL, 0.542 mmol) in DCM (5 mL), a drop of DMF was added using a Pasteur pipette. The colourless solution was stirred at room temperature for 15 min, and a solution of (3-quinoxalin-2-ylphenyl)amine (100 mg, 0.452 mmol) and diisopropylethylamine (DIEA, 90 μL, 0.542 mmol) in THF (5 mL) was added. The resulting slurry was stirred at room temperature for 24 hrs, the reaction mixture was then diluted with ethyl acetate (30 mL) and washed with water (2×25 mL), the organic phase dried over sodium sulphate and the solvent evaporated in vacuo. The resulting crude solid was purified by preparative LCMS to afford N-(3-(quinoxalin-2-yl)phenyl)but-3-enamide (35 mg, 22% yield). LCMS calculated for C18H15N3O (M+H): 290.33. found 290.24. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.59 (1H, br.), 9.52 (1H, s), 8.52 (1H, m), 8.12-8.16 (2H, m), 8.05-8.08 (1H, m), 7.80-7.95 (3H, m), 7.55-7.60 (1H, m), 5.95-6.07 (1H, m), 5.25-5.12 (2H, m), 3.18 (2H, d, J=6.2 Hz).

Provenance & Evidence