Potassium Carbonate → 7-(Cyanomethoxy)indole

HRID 1198521

Reaktionsgleichung

Reaktionsgleichung von HRID 1198521
[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) was hydrogenated at 60 psi over 10% palladium on charcoal (50 mg) for 4 hours. The catalyst was 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) was 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 was dried and evaporated and the residue was chromatographed on silica in ethyl acetate-hexane (1:2) to give a pale solid.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ff6b288abf3b4fe89119d930d2236931
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05281593

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