Water → 7-bromo-1H,2H,3H-pyrido[2,3-b][1,4]oxazine

To a 1.0 ml flask, 7-bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-2-one (100 mg, 0.436 mmol) was dissolved in tetrahydrofuran (1.0 ml). To the reaction mixture, 1.0M Lithium aluminum hydride dissolved in tetrahydrofuran (0.524 ml, 0.524 mmol) was added dropwise at 0□, and then stirred for 20 minutes. After completion of the reaction by adding water to the reaction mixture, the organic layer was extracted with ethyl acetate and the combined organic layer was washed with water and saturated saline solution, dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was recrystallized from dichloromethane and diisopropyl ether to obtain white solid (63 mg, 67%).

1. additionwas added dropwise at 0□
2. customAfter completion of the reaction
3. extractionthe organic layer was extracted with ethyl acetate
4. washthe combined organic layer was washed with water and saturated saline solution
5. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
6. filtrationfiltered
7. customevaporated under reduced pressure
8. customThe residue was recrystallized from dichloromethane and diisopropyl ether

ORD record

ord-7b2d47ee27774b37937d97dd37c1cf2e

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394792B2