HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 4-Chloro-7-(1-(tert-butoxycarbonyl)indol-2-yl)isoindolinone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | 1-(tert-Butoxycarbonyl)indole-2-boronic Acid (contains varying amounts of Anhydride) | HCID 2773302 | — |
| Reactant | 4-Chloro-7-iodoisoindolinone | HCID 68492735 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 4-Chloro-7-(1-(tert-butoxycarbonyl)indol-2-yl)isoindolinone | HCID 68487594 | 44% |
Reaction Steps
In a similar manner to Step 2 of Example 1, 4-chloro-7-iodoisoindolinone (100 mg, 0.341 mmol) was dissolved in acetonitrile (7 mL), and the solution was treated with 1-(tert-butoxycarbonyl)indol-2-boronic acid (178 mg, 0.682 mmol), palladium acetate (6.1 mg, 0.027 mmol), tri(o-tolyl)phosphine (17 mg, 0.055 mmol) and triethylamine (0.475-mL, 3.41 mmol), followed by purification by preparative thin-layer chromatography (chloroform/methanol=30/1) to obtain 4-chloro-7-(1-(tert-butoxycarbonyl)indol-2-yl)isoindolinone (57 mg, yield 44%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07745641B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-5119cba16e984a6aab5c271874fb30e8 |
| Source note | uspto-grants-2010_06 |