2,2-Difluoro-2-phenylethylamine → HCID 12147025, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-[(2-ethoxycarbonyl)ethyl]-3-bromo-6-methylpyrazinone (2-6) (0.441 g, 1.6 mmol) in toluene (15 mL) was added 2,2-difluoro-2-phenylethylamine (2-10) (0.51 g, 3.2 mmol). The resulting mixture was stirred at 110° C. for 24 hours. The mixture was diluted with ethyl acetate (100 mL) and washed with 10% hydrochloric acid (20 mL) and brine (20 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography using ethyl acetate/n-hexane (1:1) as eluent to afford the title compound (0.46 g, 81%) as a pale yellow solid. Rf 0.19 (ethyl acetate/hexane 1/1); 1H-NMR (CDCl3): δ 1.26 (t, J=7.2 Hz, 3H), 2.18 (d, J=1.2 Hz, 3H), 2.66 (t, J=6.8 Hz, 2H), 4.06 (dt, J=6.8, 14.4 Hz, 2H), 4.12 (q, J=6.8 Hz, 2H), 4.18 (t, J=7.6 Hz, 2H), 6.11 (t, J=6.4 Hz, 1H), 6.61(d, J=0.8 Hz, 1H), 7.37-7.41 (m, 3H), 7.49-7.53 (m, 2H).

Provenance & Evidence