HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Naphthol → ethyl 7-bromo-3-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Naphthol | HCID 7005 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Di-tert-butyl azodicarboxylate | HCID 97268 | — |
| Reactant | ethyl 7-bromo-3-(3-hydroxypropyl)-1H-indole-2-carboxylate | HCID 68943187 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | ethyl 7-bromo-3-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate | HCID 68938945 | — |
Reaction Steps
To a mixture of Example 1B (10.87 g), 1-naphthol (5.77 g) and triphenylphosphine (10.5 g) in THF (100 mL) was added di-tert-butyl azodicarboxylate (9.21 g). The mixture was stirred for 3 days, concentrated, redissolved in dichloromethane, washed with water and brine and dried (MgSO4), filtered and concentrated. The concentrate was purified by flash column chromatography on silica gel with 0-10% ethyl acetate in hexanes. The product was recrystallized from hexanes.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09035047B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-3ba693ad7b2b4bb29f96414849c373fb |
| Source note | uspto-grants-2015_05 |