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Potassium Acetate → 2-Methoxy-6-oxo-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindole-11-carbaldehyde

HRID 1767569
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Reaktionsgleichung

Reaktionsgleichung von HRID 1767569
I[C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[C:4]([N:6]1[C:14]2[C:9](=[N:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[C:8]([CH:17]=[O:18])=[CH:7]1)=[O:5].C([O-])(=O)C.[K+]>CN(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>[CH3:16][O:15][C:11]1[CH:12]=[CH:13][C:14]2[N:6]3[C:4](=[O:5])[C:3]4[C:19]([C:7]3=[C:8]([CH:17]=[O:18])[C:9]=2[N:10]=1)=[CH:20][CH:21]=[CH:22][CH:2]=4
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Komponenten

5

Edukt 2

HCID 517044Potassium AcetateHCID 187582411-(2-Iodobenzoyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridine-3-carbaldehyde

Produkt 1

HCID 183787022-Methoxy-6-oxo-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindole-11-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

Under an argon atmosphere, 0.49 mmol of the compound obtained in Step B, 0.2 mmol of tetrakis(triphenylphosphine)palladium(0) and 0.49 mmol of potassium acetate in 15 ml of DMF are heated at 140° C. for 3 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 and concentrated, and the residue is purified by flash chromatography over silica gel (eluant:petroleum ether/ethyl acetate) to yield the title compound.

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. customthe residue is purified by flash chromatography over silica gel (eluant:petroleum ether/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-012188a2f75743c7b008cde6a0e18ff1
Quelldatensatz
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07235550B2

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