Ethanol → HCID 67532062, compound

5-Fluoro-6-Amino-1,3-dihydro-indol-2-one 9d(2.26 g, 13.6 mmol) was dissolved in 40 mL of ethanol under stirring at room temperature. The solution was cooled down to 0° C. in an ice-water bath, and 4-fluoro-benzaldehyde (1.5 mL, 13.6 mmol) was then added to the solution. Upon completion of the addition, the reaction mixture was stirred at room temperature for 1 hour, and sodium borohydride (1.08 g, 28.5 mmol) was then added to the mixture. The reaction mixture was refluxed for 18 hours. The reaction mixture was naturally cooled down to room temperature, and iced water was added to precipitate solids. The resulting solids were filtered. The filter cake was washed with water (50 mL ×3), and purified by silica gel column chromatography to give the title compound 5-fluoro-6-(4-methyl-benzylamino)-1,3-dihydro-indol-2-one 10a (1.67 g, 45%) as a white solid.

1. temperatureThe solution was cooled down to 0° C. in an ice-water bath
2. additionUpon completion of the addition
3. stirringthe reaction mixture was stirred at room temperature for 1 hour
4. temperatureThe reaction mixture was refluxed for 18 hours
5. additionwas added
6. customto precipitate solids
7. filtrationThe resulting solids were filtered
8. washThe filter cake was washed with water (50 mL ×3)
9. custompurified by silica gel column chromatography

ORD record

ord-26a9a1a441764b45be6fa4c7024b3ba8

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299069B2