Water → N-(3-Bromo-6-chloro-2-pyridinyl)-2,2-dimethylpropanamide

Temperature

0 °C

A solution of N-(6-chloro-2-pyridinyl)-2,2-dimethylpropanamide (4.83 g, 22.7 mmol) in THF (40 ml) at −78° C. under argon was treated with n-butyl lithium (20 ml, 2.5M in Hexanes, 50 mmol) over 10 min and then allowed warm to 0° C., stirred at 0° C. for 3 h and then recooled to −78° C. The reaction was then treated dropwise with dibromoethane (2.057 ml, 23.9 mmol) and the reaction was allowed warm to rt and stirred at rt for 0.5 h. The reaction was then treated with water (5 ml), stirred at rt for 5 min, treated with more water (500 ml) and extracted with diethyl ether (3×500 ml). The organic extracts were dried (MgSO4), filtered, evaporated and the residue chromatographed (0-25% ethyl acetate:Hexane) to give the product as a yellow solid (3.489 g, 53%).

1. customrecooled to −78° C
2. temperaturethe reaction was allowed warm to rt
3. stirringstirred at rt for 0.5 h
4. stirringstirred at rt for 5 min
5. extractionextracted with diethyl ether (3×500 ml)
6. dry with materialThe organic extracts were dried (MgSO4)
7. filtrationfiltered
8. customevaporated
9. customthe residue chromatographed (0-25% ethyl acetate:Hexane)

ORD record

ord-2986a14c8a4a410aa4db2b76612024d4

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389524B2