Water → N-(3-bromo-6-chloro-2-pyridinyl)-2,2-dimethyl-N-2-propen-1-ylpropanamide

A solution of N-(3-bromo-6-chloro-2-pyridinyl)-2,2-dimethylpropanamide (2.305 g, 7.907 mmol) in DMF (40 ml) at 0° C. under argon was treated with sodium hydride (0.696 g, 17.395 mmol) and then allowed warm to rt over 0.25 h, stirred at rt for 0.25 h and then treated with allyl iodide (1.61 ml, 17.395 mmol) and stirred at rt for 1 h. The reaction was then treated with water (10 ml), concentrated to approximately 5 ml, treated with more water (200 ml) and extracted with DCM (3×200 ml). The organic extracts were dried (MgSO4), filtered, evaporated and the residue chromatographed (0-20% ethyl acetate:Hexane) to give the product as a yellow oil which solidified to an off white solid (5.324 g, 67%).

1. stirringstirred at rt for 1 h
2. concentrationconcentrated to approximately 5 ml
3. additiontreated with more water (200 ml)
4. extractionextracted with DCM (3×200 ml)
5. dry with materialThe organic extracts were dried (MgSO4)
6. filtrationfiltered
7. customevaporated
8. customthe residue chromatographed (0-20% ethyl acetate:Hexane)

ORD record

ord-8b2175346e314c0fbc270c519cbf4919

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389524B2