HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 3-[1-(4-Aminomethyl-3-hydroxybenzyl)-indol-3-yl]-4-[1-methyl-indol-3-yl]-pyrrole-2,5-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Ethyl acetate ethanol ammonium hydroxide | HCID 18433202 | — |
| Reactant | 3-[1-(4-Aminomethyl-3-(2-(trimethylsilyl)ethoxymethoxy)benzyl)-indol-3-yl]-4-[1-methyl-indol-3-yl]pyrrole-2,5-dione | HCID 22123297 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-[1-(4-Aminomethyl-3-hydroxybenzyl)-indol-3-yl]-4-[1-methyl-indol-3-yl]-pyrrole-2,5-dione | HCID 22123275 | 22.9% |
Reaction Steps
The product of Example 10 (0.068 g, 0.11 mmol) was dissolved in methylene chloride (0.5 ml). Water (0.1 mL) was added and the solution cooled on ice. Trifluoroacetic acid (1 mL) was added and the reaction allowed to proceed for 30 minutes. Extractive workup with ethyl acetate followed by chromatography (ethyl acetate/ethanol/ammonium hydroxide:90/10/2) yields 3-[1-(4-aminomethyl-3-hydroxybenzyl)-indol-3-yl]-4-[1-methyl-indol-3-yl]-pyrrole-2,5-dione (0.012 g,) as a red solid. Treatment with hydrochloric acid yields the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06153641 |
| Source dataset | uspto-grants-2000_11 |
| ORD ID | ord-527ae99b34e54cc4a24e99c1efe1da9d |
| Source note | uspto-grants-2000_11 |