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

Temperatur

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-Eintrag

ord-e5f2bf72adf34d7f83130ade1ddb5a30

Quelldatensatz

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08338415B2