Carbazole → HCID 58068390, compound

Participants

Reaction Conditions

Reaction Steps

To a 200-mL three-neck flask were added 1.6 g (5.0 mmol) of 3-(3-bromophenyl)-1,2,4-triazolo[3,4-a]isoquinoline synthesized in Step 2, 0.92 g (5.5 mmol) of 9H-carbazole, 0.16 g (0.61 mmol) of 18-crown-6-ether, 1.4 g (10 mmol) of potassium carbonate, and 3 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU). To this mixture was added 82 mg (0.43 mmol) of copper(I) iodide, and the mixture was stirred at 180° C. for 6 hours under a nitrogen stream. After the stirring, this mixture was cooled to room temperature, and chloroform was added thereto. The organic layer of the resulting mixture was washed with water, a saturated aqueous solution of sodium hydrogen carbonate and saturated brine, and the organic layer was dried over magnesium sulfate. The obtained mixture was gravity-filtered, and the filtrate was concentrated to give a solid. This solid was purified by silica gel column chromatography (toluene:ethyl acetate=5:1) to give a solid. A methanol suspension of the obtained solid was irradiated with ultrasonic waves, and the solid was collected by suction filtration. Further, this solid was recrystallized from toluene, so that the substance which was the object of the synthesis was obtained as 1.6 g of a white powder in 78% yield.

Provenance & Evidence