Hydrochloric Acid → HCID 67314653, compound

Temperature

0 °C

A solution of 5-fluoro-1,3-dihydro-indol-2-one (440 mg, 2.9 mmol.) in THF (3 mL) is cooled to 0° C. under an Argon atmosphere and treated with a solution of lithium bis(trimethylsilyl)amide (5.8 mL of a 1 M solution in THF, 5.8 mmol) dropwise. The resulting solution is stirred at 0° C. for 10 min and warmed to room temperature. A solution of 6-ethyl-6H-thieno[2,3-c]furan-4-one, (328 mg, 1.94 mmol) in THF (4 mL) and added dropwise to the reaction mixture. The resulting solution is stirred for 4 h. The reaction mixture is poured into aqueous 10% HCl solution (100 mL). The resulting mixture is heated to 90° C. for 45 min and stirred at room temperature for 36 h. The precipitate which formed is collected by filtration and dried. The solid obtained is purified by chromatography (30% EtOAc/hexane). The product containing fractions are concentrated to give the title compound as a yellow solid (190 mg, 33%).

1. temperaturewarmed to room temperature
2. stirringThe resulting solution is stirred for 4 h
3. temperatureThe resulting mixture is heated to 90° C. for 45 min
4. stirringstirred at room temperature for 36 h
5. customThe precipitate which formed
6. filtrationis collected by filtration
7. customdried
8. customThe solid obtained
9. customis purified by chromatography (30% EtOAc/hexane)
10. additionThe product containing fractions
11. concentrationare concentrated

ORD record

ord-612e8fe692b44b2296d971d523434af7

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455535B2