Dimethylformamide → HCID 87368680, compound

Temperature

-10 °C

To a solution of diisopropylamine (3.2 g, 32.4 mmol) in THF (20 mL) was added n-butyl lithium (20.2 mL, 1.6N), dropwise at −10° C. and the solution stirred for 30 min. The reaction mixture was cooled to −78° C. and into this was added, tert-butyl 6,7-difluoro-1,2-benzisoxazol-3-yl carbonate (Intermediate 530, 4.0 g, 14.7 mmol) in THF (20 mL). It was stirred at −78° C. for 2 h and then treated with dimethylformamide (3.2 g, 44.2 mmol) and continued the stirring at −78° C. for 1 hour. The reaction was quenched by the addition of saturated solution of ammonium chloride and then extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with water followed by brine and then dried over anhydrous sodium sulfate. The solution was filtered and the filtrate evaporated under vacuum, and the residue was purified over silica gel column using a gradient of ethyl acetate in pet. ether to give product as a yellow solid Yield: 3.0 g (68%).

1. temperatureThe reaction mixture was cooled to −78° C.
2. additioninto this was added
3. stirringIt was stirred at −78° C. for 2 h
4. customstirring at −78° C.
5. customfor 1 hour
6. customThe reaction was quenched by the addition of saturated solution of ammonium chloride
7. extractionextracted with ethyl acetate (2×20 mL)
8. washThe combined organic layers were washed with water
9. dry with materialdried over anhydrous sodium sulfate
10. filtrationThe solution was filtered
11. customthe filtrate evaporated under vacuum
12. customthe residue was purified over silica gel column

ORD record

ord-22b9d0eca57742c6838f22943811b415

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658641B2