Dimethylformamide → HCID 18617606, Verbindung
Reaktionsgleichung
P(Cl)(Cl)([Cl:3])=O.O[CH2:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2.CN([CH:21]=[O:22])C>>[Cl:3][CH2:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH:21]=[O:22]Komponenten
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
A solution of 1.46 mL (15.7 mmol) phosphorous oxychloride in 5 mL DMF is stirred for 20 minutes. A solution of 2.11 g (13.1 mmol) 5-(2-hydroxyethyl)indole (reference example 6) in 5 mL DMF is added, and the reaction mixture is heated to 80° C. for ten minutes. The reaction is quenched with solid sodium bicarbonate and diluted with 250 mL 1:1 CH2Cl2:MeOH. The inorganic solids are filtered off, and the filtrate concentrated. The resulting residue is refluxed in 75 mL 1N HCl solution for one hour, then extracted with CH2Cl2. The organic extracts are combined and concentrated, and the residue chromatographed (20:1 CH2Cl2:MeOH) to provide 2.45 g of the product as a brown solid in 90% yield. 1H NMR (CDCl3): δ 3.19 (2H, t, J=7 Hz), 3.76 (2H, t, J=7 Hz), 7.20 (1H, dd, J=8, 1 Hz), 7.40 (1H, d, J=8 Hz), 7.85 (1H, d, J=3 Hz), 8.19 (1H, s), 8.98 (1H, br), 10.05 (1H, s). MS (EI) m/z 207, 209 (M[35Cl, 37Cl])+, 158 (M−CH2Cl)+.
Aufarbeitung
- customThe reaction is quenched with solid sodium bicarbonate
- additiondiluted with 250 mL 1:1 CH2Cl2
- filtrationThe inorganic solids are filtered off
- concentrationthe filtrate concentrated
- temperatureThe resulting residue is refluxed in 75 mL 1N HCl solution for one hour
- extractionextracted with CH2Cl2
- concentrationconcentrated
- customthe residue chromatographed (20:1 CH2Cl2:MeOH)
Quellen und Nachweise
- ORD-Eintrag
- ord-aed3470732e144979fb4a2b68379b1a7
- Quelldatensatz
- uspto-grants-2003_04
- Patentnummer
- US06541505B1
Notizen zur Reaktion
Wird geladen…