Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Oxindole | HCID 321710 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | HCID 58478754 | HCID 58478754 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 76798884 | HCID 76798884 | 67.4% |
Reaction Steps
A solution of 1,3-dihydro-indol-2-one (650 mg, 4.77 mmol.) in THF (10 mL) is cooled to 0° C. under an argon atmosphere and treated with a solution of lithium bis(trimethylsilyl)amide (9.6 mL of a 1 M solution in THF, 9.6 mmol) dropwise. The ice bath is removed and 6-chloro-1-ethyl-1H-furo[3,4-c]pyridin-3-one (630 mg, 3.18 mmol) is added directly as a solid. The resulting solution is stirred for 4.5 h. The reaction mixture is poured into aqueous 10% HCl solution (100 mL) and stirred at room temperature for 10 min and then heated at 90-100° C. for 2 h. The reaction mixture is cooled to room temperature for 36 h during which time a precipitate formed. The precipitate which formed is collected by filtration and dried to give the title compound as an orange solid (670 mg, 67%).
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-cd6f9e17fb674daf83098845323b0341 |
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| Source note | uspto-grants-2011_07 |
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