Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | Tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate | HCID 60155786 | — |
| Reactant | HCID 178520025 | HCID 178520025 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 178452311 | HCID 178452311 | 91.4% |
Reaction Steps
The synthesis was performed with reference to the known literature (Tetrahedron, Vol. 29, p. 359, 1973). A solution of tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.100 g, 0.287 mmol) in methanol (1.2 mL) was added with 1H-indazole-3-carboxaldehyde (0.0419 g, 0.287 mmol), and piperidine (0.00244 g, 0.0287 mmol) at room temperature, and the mixture was stirred at 60° C. for 3 hours. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol) to obtain tert-butyl (Z)-4-({2-[(1H-indazol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.125 g, 91%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09156827B2 |
|---|
| Source dataset | uspto-grants-2015_10 |
|---|
| ORD ID | ord-f292859667ca4310acb1d794f70fdfac |
|---|
| Source note | uspto-grants-2015_10 |
|---|