Reaktionsgleichung
CN(C)[CH2:3][C:4]1[C:12]2[C:7](=[C:8]([N+:13]([O-:15])=[O:14])[CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.IC.[C-:19]#[N:20].[K+]>CN(C=O)C.O.C1COCC1>[N+:13]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[NH:6][CH:5]=[C:4]2[CH2:3][C:19]#[N:20])([O-:15])=[O:14]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Versuchsvorschrift
A solution of N,N-dimethyl-1-(7-nitro-1H-indol-3-yl)methanamine from Step A (3.3 g, 18.5 mmol) in DMF (3 mL), H2O (3 mL), THF (150 mL) and iodomethane (2.85 mL, 45.7 mmol) was heated at reflux for 15 min as a white precipitate formed. Potassium cyanide (6.0 g, 92.1 mmol) was added and reflux was continued for 2 h. The cooled solution was filtered and concentrated under reduced pressure and the residue was triturated with MeOH to give (7-nitro-1H-indol-3-yl)acetonitrile as a yellow solid. A suspension of this solid in MeOH (10 mL) was cooled to 0° C. and HCl (g) was bubbled in slowly for 30 min. The reaction mixture was aged for 1 h, then concentrated in vacuo. To the residue was added 6 M aqueous HCl (20 mL) and the mixture was extracted with EtOAc (3×20 mL). The combined organic extracts were washed with saturated aqueous NaHCO3 (50 mL), then brine (20 mL), dried over Na2SO4, filtered, and concentrated to give the title compound. MS: m/z=235 (M+1).
Aufarbeitung
- temperatureat reflux for 15 min as a white precipitate
- customformed
- temperaturereflux
- filtrationThe cooled solution was filtered
- concentrationconcentrated under reduced pressure
- customthe residue was triturated with MeOH
Quellen und Nachweise
- ORD-Eintrag
- ord-ee8c0ad708824b1d9b71d72dc400b640
- Quelldatensatz
- uspto-grants-2012_03
- Patentnummer
- US08133891B2
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