Sodium Bicarbonate → HCID 118080242, compound

Temperature

78 °C

A 250-mL, three-necked round bottom flask fitted with a nitrogen inlet, magnetic stir bar, thermocouple, and condenser was charged with (S)-1-(6-bromo-4-(cyclopropanecarbonyl)-2-methyl-3,4-dihydroquinoxaline-1(2H)-yl)-2,2,2-trifluoroethanone (8.26 g, 21.12 mmol), ethanol (82 mL), and half-saturated sodium bicarbonate (82 mL, 422 mmol). The reaction mixture was heated to 78° C. for 3 h and then cooled to rt. The ethanol was removed under reduced pressure, and the resulting solution was extracted with dichloromethane (2×125 mL). The combined organic layers were concentrated under reduced pressure. The crude product was diluted with 2-methyltetrahydrofuran (100 mL), and the resulting solution concentrated to remove trace water. This afforded (S)-(7-bromo-3-methyl-3,4-dihydroquinoxaline-1(2H)-yl)(cyclopropyl)methanone (6.25 g, 100%) as an oil, which was used as is for the next step. MS (ESI, pos. ion) m/z 296. [M+1]+.

1. customA 250-mL, three-necked round bottom flask fitted with a nitrogen inlet, magnetic stir bar
2. temperaturecooled to rt
3. customThe ethanol was removed under reduced pressure
4. extractionthe resulting solution was extracted with dichloromethane (2×125 mL)
5. concentrationThe combined organic layers were concentrated under reduced pressure
6. additionThe crude product was diluted with 2-methyltetrahydrofuran (100 mL)
7. concentrationthe resulting solution concentrated
8. customto remove trace water

ORD record

ord-13c83c37852840f38e88bb1d418a6020

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422281B2