Hydrochloric Acid → HCID 23114782, compound

Temperature

0 °C

To a mixture of a hexane solution (1.58M, 8.41 ml, 13.3 mmol) of n-butyl lithium and tetrahydrofuran (40 ml) was added diisopropylamine (1.86 ml, 13.3 mmol) at −78° C. After the resulting mixture was stirred at 0° C. for 1 hour, the reaction mixture was cooled to −78° C. To the reaction mixture was added a tetrahydrofuran (10 ml) solution of 5-chloro-2-(2,2,5,5-tetramethyl-1,2,5-azadisilolidin-1-yl)pyridine (3.27 g, 12.1 mmol). At the same temperature, the resulting mixture was stirred for 1 hour. Then, a tetrahydrofuran (10 ml) solution of 2,5-difluorobenzaldehyde (1.89 g, 13.3 mmol) was added to the reaction mixture. After stirring at the same temperature for 30 minutes, 1N hydrochloric acid (50 ml) was added at 0° C. To the reaction mixture was added a 1N aqueous solution (100 ml) of sodium hydroxide. The product thus obtained was extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was washed with a mixed solvent of dichloromethane/hexane, and collected by filtration to give the title compound (1.76 g, 6.50 mmol, 54%) as a white solid.

1. temperaturethe reaction mixture was cooled to −78° C
2. stirringAt the same temperature, the resulting mixture was stirred for 1 hour
3. stirringAfter stirring at the same temperature for 30 minutes
4. customThe product thus obtained
5. extractionwas extracted with diethyl ether
6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated under reduced pressure
9. customThe residue thus obtained
10. washwas washed with a mixed solvent of dichloromethane/hexane
11. filtrationcollected by filtration

ORD record

ord-7e6fe77f1f6b4d95a2786995778433c7

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932271B2