Dimethylformamide → 6-fluoro-5-methoxy-1H-indole-3-carbaldehyde

HRID 8117

Reaktionsgleichung

Reaktionsgleichung von HRID 8117
O=P(Cl)(Cl)Cl.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][C:16]=1[F:17])[NH:13][CH:12]=[CH:11]2.[OH-].[Na+].CN(C)[CH:22]=[O:23]>>[F:17][C:16]1[CH:15]=[C:14]2[C:10]([C:11]([CH:22]=[O:23])=[CH:12][NH:13]2)=[CH:9][C:8]=1[O:7][CH3:6]

Komponenten

5

Edukt 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178892306-Fluoro-5-methoxy-1H-indole

Produkt 1

HCID 220148046-fluoro-5-methoxy-1H-indole-3-carbaldehydeAusbeute 95 %

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

POCl3 (10.9 ml, 71 mmol) is added dropwise to 21 ml of dimethylformamide under N2 at 10–20° C., is stirred 15 minutes, then a 13 ml dimethylformamide solution of 5-methoxy-6-fluoro-indole (J. Med. Chem., 22:63–69, 1979; 10.7 g, 64.7 mmol) is added at a rate to keep the reaction temperature between 10 and 20° C. After the addition is complete, the mixture is stirred for 1 hour. Crushed ice and aqeuous NaOH (12.5 g/50 ml H2O) is added to reaction. The resulting mixture is heated to reflux with a heat gun for 1 minute, cooled to 10° C., and is filtered to give 11.8 g of 6-fluoro-5-methoxy-1H-indole-3-carbaldehyde (95%).

Aufarbeitung

  1. customthe reaction temperature between 10 and 20° C
  2. additionAfter the addition
  3. stirringthe mixture is stirred for 1 hour
  4. temperatureThe resulting mixture is heated
  5. temperatureto reflux with a heat gun for 1 minute
  6. filtrationis filtered

Quellen und Nachweise

ORD-Eintrag
ord-512b38c506b9498185831786eee0d90a
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087635B2

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