HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
2-(2-Aminoethyl)-5-methoxyindole → 5-(3-fluorobenzyl)-N-(2-(6-methoxy-1H-indol-3-yl)ethyl)isoxazole-3-carboxamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | 2-(2-Aminoethyl)-5-methoxyindole | HCID 17654 | — |
| Edukt | Diisopropylethylamine | HCID 81531 | — |
| Edukt | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Edukt | 5-(3-Fluorobenzyl)isoxazole-3-carboxylic acid | HCID 66832107 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | 5-(3-fluorobenzyl)-N-(2-(6-methoxy-1H-indol-3-yl)ethyl)isoxazole-3-carboxamide | HCID 66832090 | 38% |
Reaktionsschritte
A solution of the 5-(3-fluorobenzyl)isoxazole-3-carboxylic acid (0.057 g; 0.257 mmol), 2-(6-methoxy-1H-indol-3-yl)ethanamine (0.054 g; 0.284 mmol), HATU (0.108 g; 0.284 mmol) and N,N-diisopropylethylamine (0.112 mL; 0.649 mmol) in DMF (3 mL), was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulfate, the organic layer was washed with sodium carbonate, brine, dried and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.035 g (38%) of the title compound as a white solid.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US09434722B2 |
| Quelldatensatz | uspto-grants-2016_09 |
| ORD ID | ord-de9f2b2e214b4f748ffb4c945caae68a |
| Quellennotiz | uspto-grants-2016_09 |