HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-([1,1'-biphenyl]-2-ylmethyl)-2-cyclopropyl-4-methoxyl-1H-indole → 1-([1,1'-biphenyl]-2-ylmethyl)-2-cyclopropyl-4-hydroxy-1H-indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-([1,1'-biphenyl]-2-ylmethyl)-2-cyclopropyl-4-methoxyl-1H-indole | HCID 10546013 | — |
| Reactant | Boron tribromide dichloromethane | HCID 22277759 | — |
| Product | 1-([1,1'-biphenyl]-2-ylmethyl)-2-cyclopropyl-4-hydroxy-1H-indole | HCID 10617069 | 29.2% |
Reaction Steps
By the method used in Example 1, Part D, 1.25 g (3.7 mmol) of 1-([1,1'-biphenyl]-2-ylmethyl)-2-cyclopropyl-4-methoxyl-1H-indole was O-demethylated by treating it with 15 mL of 1M BBr3 /CH2Cl2. The crude product was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 367 mg (29% yield) of 1-([1,1'-biphenyl]-2-ylmethyl)-2-cyclopropyl-4-hydroxy-1H-indole as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05654326 |
| Source dataset | uspto-grants-1997_08 |
| ORD ID | ord-762d7f5a4cbd435681ca193c56afa614 |
| Source note | uspto-grants-1997_08 |