Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | 5-fluoro-1,3-dihydro-2H-indol-2-one | HCID 3731012 | — |
| Reactant | HCID 58478742 | HCID 58478742 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67315497 | HCID 67315497 | 3% |
Reaction Steps
A solution of 5-fluoro-1,3-dihydro-indol-2-one (340 mg, 2.25 mmol.) in THF (3 mL) is cooled to 0° C. under an Argon atmosphere and treated with a solution of lithium bis(trimethylsilyl)amide (4.5 mL of a 1 M solution in THF, 4.5 mmol) dropwise. The resulting solution is stirred at 0° C. for 10 min and then warmed to room temperature. A solution of 6-phenyl-6H-thieno[2,3-c]furan-4-one, (320 mg, 1.5 mmol) in THF (6 mL) is added dropwise to the reaction mixture. The resulting solution is stirred for 4 h. and then poured into aqueous 10% HCl solution (50 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 (silica gel, ethyl acetate/hexane) to give the title compound as a yellow solid (15 mg, 3%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07977351B2 |
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| Source dataset | uspto-grants-2011_07 |
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| ORD ID | ord-dfcad5002eeb463e8aa514120720565a |
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| Source note | uspto-grants-2011_07 |
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