Diisopropylethylamine → 2-chloro-N-(3-(quinoxalin-2-yl)phenyl)propanamide

Participants

Reaction Steps

To a solution of (3-quinoxalin-2-ylphenyl)amine (124 mg, 0.560 mmol) and diisopropylethylamine (DIEA, 111 μL, 0.672 mmol) in THF (5 mL), 2-chloropropionyl chloride (60 μL, 0.620 mmol) was added at room temperature. The reaction mixture was stirred at room temperature for 24 hrs and then diluted with ethyl acetate (20 mL). The organic phase was washed with water (20 mL), dried over MgSO4 and the solvent was evaporated in vacuo to afford 2-chloro-N-(3-(quinoxalin-2-yl)phenyl)propanamide (92 mg, 52% yield). LCMS calculated for C17H14ClN3O (M+H): 312.77. found 313. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.52 (1H, br.), 9.53 (1H, s), 8.55 m), 8.12-8.18 (2H, m), 8.05-8.08 (1H, m), 7.82-7.95 (3H, m), 7.55-7.60 (1H, m), 4.75 (1H, q, J=6.8 Hz), 1.68 (3H, d, J=6.8 Hz).

Provenance & Evidence