Sodium Azide → Propyl (7-azido-4-fluoro-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate
Reaktionsgleichung
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]1[CH2:11][CH:12](OS(C)(=O)=O)[CH2:13][CH2:14][C:8]1=[C:7]2[CH2:20][C:21]([O:23][CH2:24][CH2:25][CH3:26])=[O:22].[N-:27]=[N+:28]=[N-:29].[Na+]>CN(C=O)C>[N:27]([CH:12]1[CH2:11][N:9]2[C:10]3[C:6]([C:7]([CH2:20][C:21]([O:23][CH2:24][CH2:25][CH3:26])=[O:22])=[C:8]2[CH2:14][CH2:13]1)=[CH:5][CH:4]=[CH:3][C:2]=3[F:1])=[N+:28]=[N-:29]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
To a stirred solution of propyl {4-fluoro-7-[(methylsulfonyl)oxy]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl}acetate (1 eq) in DMF (0.15M) at 0° C. was added sodium azide (1.2 eq). The reaction mixture was stirred at 60° C. for 6 h. The reaction was quenched by addition of water and NH4Cl, extracted with EtOAc, washed with water, brine, dried and evaporated. The residue was purified by column chromatography on silica gel eluting with EtOAc/Hexanes (0 to 50%) to give the desired material as a yellow oil.
Aufarbeitung
- customThe reaction was quenched by addition of water and NH4Cl
- extractionextracted with EtOAc
- washwashed with water, brine
- customdried
- customevaporated
- customThe residue was purified by column chromatography on silica gel eluting with EtOAc/Hexanes (0 to 50%)
Quellen und Nachweise
- ORD-Eintrag
- ord-d3e80184fdcd4a93a52ef8e7e3e447ac
- Quelldatensatz
- uspto-grants-2013_03
- Patentnummer
- US08394819B2
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