Acetamide → HCID 67309142, compound

HRID 1877445Notes

Reaction equation

HRID 1877445 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[C:20](Br)[CH:19]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[C:27]([NH2:30])(=[O:29])[CH3:28].CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.[Cu](I)I.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[C:20]([NH:30][C:27](=[O:29])[CH3:28])[CH:19]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

8

Reactant 4

HCID 178AcetamideHCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 67309163HCID 67309163, compound

Product 1

HCID 67309142HCID 67309142, compoundYield 54.2%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

In a microwave reactor, a mixture of 1.015 g of 9-(3-bromo-4-cyanophenyl)-9H-carbazole-4-carboxylic acid methyl ester, obtained according to stage 3 of Example 1, 444 mg of acetamide, 71 mg of trans-N,N′-dimethylcyclohexane-1,2-diamine, 1.039 g of potassium carbonate and 95 mg of copper iodide in 20 ml of dioxane is heated at 160° C. for 1.5 hours. The reaction medium is poured into 200 ml of ethyl acetate. The organic phase is washed with 100 ml of a saturated solution of sodium bicarbonate. The aqueous phase is re-extracted with twice 100 ml of ethyl acetate. The combined organic phases are washed with twice 50 ml of a saturated solution of sodium bicarbonate and once with 100 ml of a saturated solution of sodium chloride, dried over magnesium sulphate and evaporated to dryness under vacuum. The residue is chromatographed on silica gel (40-63 μm), elution being carried out with pure dichloromethane. 520 mg of 9-(3-acetylamino-4-cyanophenyl)-9H-carbazole-4-carboxylic acid methyl ester are obtained in the form of an off-white solid, the characteristics of which are the following:

Workup

  1. customobtained
  2. washThe organic phase is washed with 100 ml of a saturated solution of sodium bicarbonate
  3. extractionThe aqueous phase is re-extracted with twice 100 ml of ethyl acetate
  4. washThe combined organic phases are washed with twice 50 ml of a saturated solution of sodium bicarbonate and once with 100 ml of a saturated solution of sodium chloride
  5. dry with materialdried over magnesium sulphate
  6. customevaporated to dryness under vacuum
  7. customThe residue is chromatographed on silica gel (40-63 μm), elution

Sources & evidence

ORD record
ord-b0d12a489d8946ac9d713f6436b1fc80
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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