Potassium Carbonate → HCID 66838970, compound

HRID 546741Notes

Reaction equation

HRID 546741 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+].[CH:23]([N:26]([CH:38]([CH3:40])[CH3:39])[C:27]([C:29]1[CH:34]=[C:33]([O:35][CH3:36])[C:32](I)=[CH:31][N:30]=1)=[O:28])([CH3:25])[CH3:24]>CN(C=O)C.[Cu](I)I.C(OCC)(=O)C>[CH:38]([N:26]([CH:23]([CH3:25])[CH3:24])[C:27]([C:29]1[CH:34]=[C:33]([O:35][CH3:36])[C:32]([N:5]2[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]2)=[CH:31][N:30]=1)=[O:28])([CH3:40])[CH3:39]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 11473918HCID 11473918, compoundHCID 178418800HCID 178418800, compound

Product 1

HCID 66838970HCID 66838970, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

4-Methyl-1H-imidazole (680 mg), copper iodide (78.8 mg), trans-1,2-bis(methylamino)cyclohexane (0.265 mL) and potassium carbonate (2.52 g) were added to a solution of 5-iodo-4-methoxypyridine-2-carboxylic acid diisopropylamide synthesized according to the method in Organic Letters, 2002, vol. 4, p. 2385 (3 g) in DMF (10 mL). The reaction solution was stirred in a sealed tube at 110° C. for 20 hours. The reaction solution was left to cool to room temperature, and ethyl acetate was added. The insoluble matter was removed by filtration through celite. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 881 mg of the title compound. The property value of the compound is as follows.

Workup

  1. customsynthesized
  2. waitThe reaction solution was left
  3. temperatureto cool to room temperature
  4. customThe insoluble matter was removed by filtration through celite
  5. washThe resulting organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-7fcb536ac40a44ed97f7524491b12195
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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