Water → N-(6-Bromopyridin-2-yl)-2,2-dimethylpropanamide

Temperature

0 °C

4.0 g (23.1 mmol) of 6-bromo-2-aminopyridine from example 14.1 were dissolved in 25 ml of dichloromethane and admixed with 4.1 ml (2.92 g, 28.9 mmol) of triethylamine. After cooling to 0° C., a solution of 3.1 ml (3.06 g, 25.4 mmol) of pivaloyl chloride in 5.0 ml of dichloromethane was added dropwise over a period of 10 min. The reaction mixture was allowed to warm to room temperature overnight and, for workup, poured onto 100 ml of dist. H2O. The phases were separated, the aqueous phase was extracted twice with 100 ml each time of ethyl acetate and the combined organic phases were dried over Na2SO4. The solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane and filtered through a short silica gel column (3×10 cm). After the solvent had been removed under reduced pressure, 5.73 g (22.3 mmol, 96.5%) of 6-bromo-2-pivaloylaminopyridine were obtained as a white solid.

1. temperatureto warm to room temperature overnight and, for workup
2. additionpoured onto 100 ml of dist
3. customThe phases were separated
4. extractionthe aqueous phase was extracted twice with 100 ml each time of ethyl acetate
5. dry with materialthe combined organic phases were dried over Na2SO4
6. customThe solvent was removed under reduced pressure
7. dissolutionthe residue was dissolved in dichloromethane
8. filtrationfiltered through a short silica gel column (3×10 cm)
9. customAfter the solvent had been removed under reduced pressure

ORD record

ord-d6f804a575d54f4985d63b7a64de7493

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07049473B2