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

HRID 433060Notes

Reaction equation

HRID 433060 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31374DimethylacetamideSolvent

Procedure

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.

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. custompurified by flash chromatography over silica gel (eluant:petroleum ether/ethyl acetate, 8:2)

Sources & evidence

ORD record
ord-45e1783439104a798d4b56ff8d4b6548
Source dataset
uspto-grants-2003_12
Patent number
US06667304B2

Reaction notes

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