Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Trifluoroacetic acid | HCID 6422 | — |
| Edukt | Sodium cyanoborohydride | HCID 5003444 | — |
| Edukt | ethyl 4-{7-[5-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl]-1H-indol-3-yl}-4-oxobutanoate | HCID 59146159 | — |
| Lösungsmittel | Ethanol | HCID 702 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | HCID 59146155 | HCID 59146155 | 51,5% |
Reaktionsschritte
To a solution of ethyl 4-{7-[5-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl]-1H-indol-3-yl}-4-oxobutanoate (D52) (300 mg) and TFA (5 mL) in ethanol (15 mL) and DCM (15 mL) was added sodium cyanoborohydride (235 mg) in portions. The reaction mixture was stirred at 20° C. for 4 days. The mixture was diluted with DCM (30 mL) and washed with water. The organic phase was separated and dried over anhydrous sulphate. After filtration, the solvent was evaporated to give the crude product, which was purified by preparative TLC separation to afford ethyl 4-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]butanoate (D53) as a white solid (150 mg). MS (ES): C25H26ClN3O4 requires 467; found 468.2 (M+H+).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08217028B2 |
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| Quelldatensatz | uspto-grants-2012_07 |
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| ORD ID | ord-c96a6c5a025a4e719ba4450848d90089 |
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| Quellennotiz | uspto-grants-2012_07 |
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