HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Sodium hydride → 1h-Indole-3-acetic acid,5-methoxy-2-methyl-1-[[4-(methylthio)phenyl]methyl]-,methyl ester
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Sodium hydride | HCID 24758 | — |
| Edukt | 1-(Chloromethyl)-4-(methylthio)benzene | HCID 70128 | — |
| Edukt | methyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate | HCID 82067 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | 1h-Indole-3-acetic acid,5-methoxy-2-methyl-1-[[4-(methylthio)phenyl]methyl]-,methyl ester | HCID 76850770 | 48,6% |
Reaktionsschritte
To the indole of Example 7, Step 1, (1.00 g, 4.29 mmol) in DMF (15.0 mL) at 0° C. were added NaH 60% in oil (188 mg, 4.72 mmol) and a solution of 4-chloromethylthioanisole (810 mg, 4.7 mmol) in DMF (5.0 mL). After a period of 5 min at r.t., the reaction was quenched by the addition of 25% aqueous solution of NH4OAc. The reaction was extracted with EtOAc, dried over Na2SO4, evaporated in vacuo and purified by flash chromatography (20% EtOAc in hexane) to provide the title compound (770 mg).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US05639780 |
| Quelldatensatz | uspto-grants-1997_06 |
| ORD ID | ord-a915ee5f0f4549feb05435c9c9d1ea7b |
| Quellennotiz | uspto-grants-1997_06 |