Water → HCID 118080147, compound

Temperature

60 °C

A mixture of 3-fluoro-4-nitropyridine (0.400 mL, 4.05 mmol), (S)-2-aminopropane-1-ol (0.347 mL, 4.46 mmol) and potassium carbonate (0.616 g, 4.46 mmol) in DMF (5.0 mL) was stirred at 60° C. for 2 h. Water was added and the mixture stirred at room temperature to afford a precipitate. The mixture was filtered to afford an orange solid. The filtrate was extracted with dichloromethane. The organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtrate, and concentrated to afford an orange solid. The solids were combined and purified via column chromatography on silica gel (Biotage 50 g column, gradient elution with 0-10% methanol-dichloromethane) to afford (S)-2-(4-nitropyridin-3-ylamino)propane-1-ol (0.668 g, 84%) as an orange solid. MS (ESI, pos. ion) m/z 198.

1. stirringthe mixture stirred at room temperature
2. customto afford a precipitate
3. filtrationThe mixture was filtered
4. customto afford an orange solid
5. extractionThe filtrate was extracted with dichloromethane
6. washThe organic extracts were washed with brine
7. dry with materialdried over anhydrous sodium sulfate, filtrate
8. concentrationconcentrated
9. customto afford an orange solid
10. custompurified via column chromatography on silica gel (Biotage 50 g column, gradient elution with 0-10% methanol-dichloromethane)

ORD record

ord-ff32f6fd73ae4039ab55e19f9850a308

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422281B2