Carbon tetrabromide → HCID 12147027, compound

Participants

Reaction Steps

To a magnetically stirred solution of 3-(2,2-difluoro-2-phenylethylamino)-1-(3-hydroxypropyl)-6-methylpyrazinone (2-12) (0.267 g, 0.82 mmol) and carbon tetrabromide (0.328 g, 0.99 mmol) in dichloromethane (10 mL), was added triphenylphosphine (0.26 g, 0.99 mmol) portionwise with ice-bath cooling. After the addition was complete, the mixture was stirred for an additional 2 hours. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography using ethyl acetate/n-hexane (2:1 to 1:1 gradient) as eluent to afford the title compound (0.309 g, 96.9%) as a yellow solid. Rf 0.45 ((EtOAc/hexane 1/1); 1H-NMR (CDCl3): δ 2.20 (d, J=1.2 Hz, 3H), 2.19-2.26 (m, 2H), 3.44 (t, J=6.4 Hz, 2H), 4.01-4.10 (m, 4H 6.12 (t, J=6.4 Hz, 1H), 6.62(d, J=1.2 Hz, 1H), 7.37-7.41 (m, 3H), 7.50-7.53 (m, 2H).

Provenance & Evidence