Triethylamine → HCID 86624813, compound

Temperature

0 °C

A 250 ml round bottom flask containing 1-(5-fluoro-6-methylpyridin-2-yl)ethanol (Method 14; 550 mg, 3.54 mmol) was charged with triethylamine (0.75 ml, 5.4 mmol) and anhydrous DCM (8.0 ml). The solution was cooled to 0° C., and methanesulfonyl chloride (0.32 ml, 4.1 mmol) was added dropwise. The resulting mixture was allowed to stir at room temperature for 2 hours, and the volatile components were removed using a rotary evaporator. The residue was treated with sodium azide (466 mg, 7.17 mmol) and anhydrous DMF (5.0 ml), and the slurry was allowed to stir at room temperature. After 2 hours, the mixture was partitioned between EtOAc and H2O. The aqueous phase was extracted with EtOAc, and the combined organics were washed with brine, dried, filtered, and concentrated. The crude material was purified by silica gel chromatography (Rf in 90:10 hexanes:EtOAc=0.47) to afford the title compound as a colourless oil (567 mg, 89%).

1. customthe volatile components were removed
2. customa rotary evaporator
3. stirringto stir at room temperature
4. waitAfter 2 hours
5. customthe mixture was partitioned between EtOAc and H2O
6. extractionThe aqueous phase was extracted with EtOAc
7. washthe combined organics were washed with brine
8. customdried
9. filtrationfiltered
10. concentrationconcentrated
11. customThe crude material was purified by silica gel chromatography (Rf in 90:10 hexanes:EtOAc=0.47)

ORD record

ord-fbf1498ff36049b08cf047fec8bf57fc

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08114989B2