Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 5-Methylindole | HCID 11978 | — |
| Catalyst | HCID 178419072 | HCID 178419072 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | HCID 85652382 | HCID 85652382 | — |
Reaction Steps
5-Methylindole (730.6 mg, 5.57 mmol, 1.0 eq.) was combined with the title C compound of Example 1 (3.189 g, 13.9 mmole, 2.5 eq.) and copper(I)oxide (797 mg, 5.57 mmol, 1.0 eq.) in pyridine (5.6 ml, 1M). The reaction was heated at 120° C. for 3 hours, cooled to room temperature, diluted with ethyl acetate and filtered through celite. The filtrate was washed twice with water, twice with aqueous 1N hydrochloric acid, and once with aqueous saturated sodium hydrogen carbonate. The organic phase was then dried over sodium sulfate, filtered through magnesium sulfate and concentrated. The residue was chromatographed on silica gel (50 g) eluting with hexane:ether (40:1) followed by (20:1) to give 848 mg of the title A compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05374615 |
|---|
| Source dataset | uspto-grants-1994_12 |
|---|
| ORD ID | ord-8196f4bb942f45e0a3bb5c09ea1a594a |
|---|
| Source note | uspto-grants-1994_12 |
|---|