Pyridine → HCID 118078957, compound

Temperature

0 °C

A 250-mL, three-necked, round bottomed flask fitted with a nitrogen inlet, magnetic stir bar, and thermocouple was charged with (S)-1-(6-bromo-2-methyl-3,4-dihydroquinoxalin-1(2H)-yl)-2,2,2-trifluoroethanone (7.0 g, 21.66 mmol), dichloromethane (140 mL), and pyridine (2.63 mL, 32.5 mmol). The mixture was cooled to 0° C. and cyclopropanecarbonyl chloride (2.36 mL, 26.0 mmol) was slowly added while maintaining the internal temperature below 7° C. The reaction mixture was stirred cold for 30 min. and then warmed to rt. The reaction mixture was washed with 1 M aqueous HCl solution (25 mL) and water (25 mL), and the combined organic layers were concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 4:1 hexanes-ethyl acetate) to afford (S)-1-(6-bromo-4-(cyclopropanecarbonyl)-2-methyl-3,4-dihydroquinoxaline-1(2H)-yl)-2,2,2-trifluoroethanone (8.26 g, 97%) as an off-white solid. MS (ESI, pos. ion) m/z 392 [M+1]+.

1. customA 250-mL, three-necked, round bottomed flask fitted with a nitrogen inlet, magnetic stir bar
2. temperaturewhile maintaining the internal temperature below 7° C
3. temperaturewarmed to rt
4. washThe reaction mixture was washed with 1 M aqueous HCl solution (25 mL) and water (25 mL)
5. concentrationthe combined organic layers were concentrated under reduced pressure
6. customThe crude product was purified by column chromatography on silica gel (eluting with 4:1 hexanes-ethyl acetate)

ORD record

ord-36a3dae008ee4c72ac8afc359a752a7d

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422281B2