Acetamide → HCID 67309142, compound

Participants

Reaction Conditions

Reaction Steps

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:

Provenance & Evidence