Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | tert-Butyl piperazine-1-carboxylate | HCID 143452 | — |
| Reactant | HCID 44554577 | HCID 44554577 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 86681939 | HCID 86681939 | 33% |
Reaction Steps
A solution of (Z)-2-[(5-bromo-1H-indol-3-yl)methylene]-6-hydroxybenzofuran-3(2H)-one (0.30 g, 0.84 mmol) in ethanol (3.0 mL) was added with 1-tert-butoxycarbonylpiperazine (0.17 g, 0.93 mmol), and 37% aqueous formaldehyde (0.093 g, 1.1 mmol), and the mixture was stirred overnight at 50° C. in a sealed tube. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10)) to obtain tert-butyl (Z)-4-({2-[(5-bromo-1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}-methyl)piperazine-1-carboxylate (0.15 g, 33%).
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-9da3361f00d24e6b835ea9e27100dc83 |
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| Source note | uspto-grants-2015_10 |
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