Potassium Carbonate → 7-(Cyanomethoxy)indole

HRID 54523

Reaktionsgleichung

Reaktionsgleichung von HRID 54523
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[CH:14]2)[C:2]1C=CC=CC=1.BrCC#[N:21].C(=O)([O-])[O-].[K+].[K+]>CO.[Pd].C(C(C)=O)C>[C:2]([CH2:1][O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[CH:14]2)#[N:21]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 2607987-(Benzyloxy)-1H-indole

Produkt 1

HCID 150540207-(Cyanomethoxy)indole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A solution of 7-benzyloxyindole (0.5 g, 2.24 mmol) in methanol (100 ml) is hydrogenated at 60 psi (4.38 Kg/cm2) over 10% palladium on charcoal (50 mg) for 4 hours. The catalyst is filtered off and the filtrate was evaporated. A stirred solution of the residue and bromoacetonitrile (0.16 ml, 2.3 mmol) in methyl ethyl ketone (5 ml) is heated under reflux with solid anhydrous potassium carbonate (0.62 g, 4.5 mmol) for 2 hours, cooled, poured onto ice-hydrochloric acid and extracted with dichloromethane. The extract is dried and evaporated and the residue is chromatographed on silica in ethyl acetate-hexane (1:2) to give a pale solid.

Aufarbeitung

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate was evaporated
  3. temperaturecooled
  4. additionpoured onto ice-hydrochloric acid
  5. extractionextracted with dichloromethane
  6. customThe extract is dried
  7. customevaporated
  8. customthe residue is chromatographed on silica in ethyl acetate-hexane (1:2)
  9. customto give a pale solid

Quellen und Nachweise

ORD-Eintrag
ord-789f5e4231b743ab97a172bf33b31729
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622969

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