HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phthalimide → 2-[4-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)-pentyl]-isoindole-1,3-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phthalimide | HCID 6809 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | 4-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)-pentan-1-ol | HCID 23511407 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-[4-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)-pentyl]-isoindole-1,3-dione | HCID 23511400 | 66% |
Reaction Steps
To a solution of 4-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)-pentan-1-ol (1 eq) in THF (20 mL) was added dropwise diethyl azodicarboxylate (1.1 eq), triphenyl phosphine (1.1 eq) and phtalimide (1.1 eq). The yellow solution was stirred at room temperature overnight and the solution was concentrated. The crude product was directly purified by flash chromatography using a solvent gradient of 97% DCM, 3% MeOH and 0.1% TEA to yield 2-[4-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)-pentyl]-isoindole-1,3-dione (66%). MH+(375).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06756359B2 |
| Source dataset | uspto-grants-2004_06 |
| ORD ID | ord-3d06fd0df1c24300ba3e19f032d3333a |
| Source note | uspto-grants-2004_06 |