Ethanol → HCID 67532062, compound

Participants

Reaction Steps

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.

Provenance & Evidence