Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Methyl iodide | HCID 6328 | — |
| Edukt | Sodium hydride | HCID 24758 | — |
| Edukt | (6-Benzyloxy-1H-indol-3-yl)-oxo-acetic acid methyl ester | HCID 34181007 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | HCID 67272990 | HCID 67272990 | 24,1% |
Reaktionsschritte
A 0° C. suspension of (6-benzyloxy-1H-indol-3-yl)-oxo-acetic acid methyl ester (2.70 g, 8.73 mmol) in dimethylformamide (25 mL) is treated with sodium hydride (437 mg, 10.9 mmol). The mixture is stirred at 0° C. for 20 minutes. Methyl iodide (1.00 mL; 16.1 mmol) is added. The reaction mixture is stirred at 0° C. for 30 minutes and quenched with water (100 mL). The mixture is extracted with EtOAc (50 mL×2). The combined organic layers are dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product is purified by flash chromatography eluting with 60% EtOAc/Hexanes. The appropriate fractions are combined and concentrated under reduced pressure to afford the title compound (0.68 g, 24%). ES.MS m/e 324.0 (M+1).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US07863302B2 |
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| Quelldatensatz | uspto-grants-2011_01 |
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| ORD ID | ord-1f922edc966447e9852169d0bed6bd28 |
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| Quellennotiz | uspto-grants-2011_01 |
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