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

HRID 2298776Notes

Reaction equation

HRID 2298776 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-d9bb0e8f4e0142d1bad3f2e484b93e65
Source dataset
uspto-grants-2002_12
Patent number
US06495543B1

Reaction notes

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