Potassium Acetate → 2-Methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindole

HRID 433060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 433060
Br[C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[N:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1.C([O-])(=O)C.[K+]>CN(C)C(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:15][O:14][C:10]1[CH:11]=[CH:12][C:13]2[N:5]3[CH2:4][C:3]4[C:16]([C:6]3=[CH:7][C:8]=2[N:9]=1)=[CH:17][CH:18]=[CH:19][CH:2]=4

Komponenten

5

Edukt 2

HCID 517044Potassium AcetateHCID 178207361-(2-Bromobenzyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridine

Produkt 1

HCID 183786982-Methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

Under an inert atmosphere, 500 mg (1.57 mmol) of the compound obtained in Step C, 88 mg (78.9 μmol) of tetrakis(triphenylphosphine)palladium (0) and 155 mg (1.57 mmol) of potassium acetate in 15 ml of N,N-dimethylacetamide are heated at 160° C., for 2 hours. After returning to room temperature, the reaction mixture is filtered using a Büchner funnel and then evaporated to dryness. The residue is then hydrolysed and subsequently extracted with ethyl acetate. The organic phase is dried over magnesium sulphate, concentrated and purified by flash chromatography over silica gel (eluant:petroleum ether/ethyl acetate, 8:2) to yield the title compound in the form of a brown solid.

Aufarbeitung

  1. customAfter returning to room temperature
  2. filtrationthe reaction mixture is filtered
  3. customevaporated to dryness
  4. extractionhydrolysed and subsequently extracted with ethyl acetate
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. concentrationconcentrated
  7. custompurified by flash chromatography over silica gel (eluant:petroleum ether/ethyl acetate, 8:2)

Quellen und Nachweise

ORD-Eintrag
ord-45e1783439104a798d4b56ff8d4b6548
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06667304B2

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