6-fluoro-2,3-dihydro-1H-indol-2-one → 3-(4-bromo-5H-furan-2-ylidene)-6-fluoro-1,3-dihydro-indol-2-one

Temperature

0 °C

To a 0° C. stirred solution of 6-fluorooxindole (370 mg, 2.45 mmol) in anhydrous THF (10 mL) was added 1M LiHMDS/THF solution (4.9 mL, 4.9 mmol). The mixture was stirred at 0° C. for 10 minutes. 4-Bromo-5H-furan-2-one (200 mg, 1.23) was added as a solution in 2 mL of THF. The resulting mixture was stirred at 0° C. for 30 minutes, then at room temperature for 1 hour and quenched with 10 mL of 2M HCl. Methanol (5 mL) was added and the mixture was stirred at 50° C. for 0.5 hour. The mixture was poured into 150 mL of water and then stirred for 30 minutes. The precipitates were filtered, washed with water, and dried in vacuum to give 3-(4-bromo-5H-furan-2-ylidene)-6-fluoro-1,3-dihydro-indol-2-one as a yellow solid. Yield: 228 mg, 63%.

1. stirringThe resulting mixture was stirred at 0° C. for 30 minutes
2. waitat room temperature for 1 hour
3. customquenched with 10 mL of 2M HCl
4. additionMethanol (5 mL) was added
5. stirringthe mixture was stirred at 50° C. for 0.5 hour
6. additionThe mixture was poured into 150 mL of water
7. stirringstirred for 30 minutes
8. filtrationThe precipitates were filtered
9. washwashed with water
10. customdried in vacuum

ORD record

ord-ea051f6b120a48f1baf1202b2458ae29

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367664B2