Acetylacetone → 1-(2-Methyl-4-thiophen-2-yl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl)-ethanone
Reaktionsgleichung
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)=O.[CH3:18][C:19](=O)[CH2:20][C:21](=[O:23])[CH3:22]>C(O)(=O)C.S(=O)(=O)(O)O>[CH3:18][C:19]1[N:1]=[C:2]2[S:6][C:5]3[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=3[C:3]2=[C:11]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[C:20]=1[C:21](=[O:23])[CH3:22]Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
To a stirred solution of 50 mg (0.19 mmol) (2-amino-4,5,6,7-tetrahydro-benzo[b]thiophen-3-yl)-thiophen-2-yl-methanone (the preparation of which is described in example 6) in 1.5 ml acetic acid was added 0.020 ml (0.21 mmol) of pentane-2,4-dione and one drop of sulfuric acid. The mixture was then stirred at 100° C. for 10 minutes in a microwave and then concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 9:1) afforded 46 mg (74%) 1-(2-methyl-4-thiophen-2-yl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl)-ethanone as a yellow oil. ES-MS m/e (%): 328 (M+H+, 100).
Aufarbeitung
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-9502993f65864353bcc271fbbbe12fd1
- Quelldatensatz
- uspto-grants-2008_06
- Patentnummer
- US07390903B2
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