Water → 3-(3-Fluoropyrazin-2-yl)cyclohex-2-enone

Temperature

80 °C

2-Fluoro-3-iodopyrazine (2.5 g, 11.16 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-2-enone (3.10 g, 13.95 mmol), and sodium carbonate (3.55 g, 33.5 mmol) were suspended in DME (20 ml) and distilled water (5 ml). Argon was bubbled through the resulting mixture for 3 minutes, and dichlorobis(triphenylphosphino)palladium (ii) (0.431 g, 0.614 mmol) was added. The resulting mixture was stirred at 80° C. for 16 hours, the reaction was cooled to RT, and water (200 ml) was added. The resulting mixture was concentrated under reduced pressure and was extracted with EtOAc (3×200 ml). The combined organic layers were washed with brine and dried over sodium sulfate. Filtration and concentration under reduced pressure, followed by flash chromatography on silica gel (0% to 20% EtOAc in hexanes) afforded 3-(3-fluoropyrazin-2-yl)cyclohex-2-enone as a light yellow solid. MS (ESI, pos. ion) m/z: 193.1 (M+1).

1. distillationdistilled water (5 ml)
2. customArgon was bubbled through the resulting mixture for 3 minutes
3. temperaturethe reaction was cooled to RT
4. concentrationThe resulting mixture was concentrated under reduced pressure
5. extractionwas extracted with EtOAc (3×200 ml)
6. washThe combined organic layers were washed with brine
7. dry with materialdried over sodium sulfate
8. filtrationFiltration and concentration under reduced pressure

ORD record

ord-2ed456d267594b62bb14ab0d80789672

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08329700B2