HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phthalimide → 2-((4,5-Bis(4-methoxybenzyloxy)pyridin-2-yl)methyl)isoindoline-1,3-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phthalimide | HCID 6809 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | 6-Hydroxymethyl-3,4-bis[(p-methoxybenzyl)oxy]-pyridine | HCID 15662506 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-((4,5-Bis(4-methoxybenzyloxy)pyridin-2-yl)methyl)isoindoline-1,3-dione | HCID 89851933 | 55% |
Reaction Steps
To a solution of (4,5-bis(4-methoxybenzyloxy)pyridin-2-yl)methanol (Intermediate 63, 1.5 g, 3.93 mmol), phthalimide (0.579 g, 3.93 mmol) and triphenylphosphine (1.028 g, 3.93 mmol) in THF (15 mL) at room temperature was added diisopropyl azodicarboxylate (2.091 mL, 10.62 mmol). The reaction was stirred at room temperature overnight then concentrated onto silica gel. Silica gel chromatography (0%-70% ethyl acetate) afforded the title compound as a light brown solid (1.1 g, 55%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09309245B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-e49898efbc684971bc735b83cb03239a |
| Source note | uspto-grants-2016_04 |