Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | HCID 71278653 | HCID 71278653 | — |
| Reactant | HCID 178520025 | HCID 178520025 | — |
| Catalyst | Piperidine | HCID 8082 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 178437259 | HCID 178437259 | 56.6% |
Reaction Steps
A solution of tert-butyl 4-[1-(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)ethyl]piperazine-1-carboxylate (0.11 g, 0.30 mmol) in methanol (5.0 mL) was added with 1H-indazole-3-carboxaldehyde (0.040 g, 0.27 mmol). Then, the mixture was added with 7 drops of piperidine, and the mixture was stirred at 50° C. for 1 hour. The reaction mixture was added with toluene, then the solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (95:5)) to obtain tert-butyl (Z)-4-{1-[2-(1H-indazol-3-yl)methylene-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl]ethyl}piperazine-1-carboxylate (0.075 g, 51%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09156827B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-2264cb1e967e4fa7b4f0d357b53a171e |
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| Source note | uspto-grants-2015_10 |
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