Potassium Acetate → HCID 18378699, compound

HRID 2298761Notes

Reaction equation

HRID 2298761 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[N:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[CH:13]=[CH:12]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>[CH3:21][O:20][C:16]1[CH:17]=[CH:18][C:19]2[N:11]3[CH2:10][CH2:9][CH2:8][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[C:12]3=[CH:13][C:14]=2[N:15]=1

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 18758222HCID 18758222, compound

Product 1

HCID 18378699HCID 18378699, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31374DimethylacetamideSolvent

Procedure

Under an inert atmosphere, 500 mg (1.45 mmol) of the compound obtained in Step A, 81 mg (72.5 μmol) of tetrakis(triphenylphosphine)palladium(0) and 142 mg (1.45 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, 9:1) to yield the title compound in the form of a colourless oil.

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, 9:1)

Sources & evidence

ORD record
ord-e8834d8919324700b59b6f9a5f1ddeab
Source dataset
uspto-grants-2002_12
Patent number
US06495543B1

Reaction notes

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