Carbazole → HCID 58068390, compound

HRID 574037Notes

Reaction equation

HRID 574037 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:12]3[CH:13]=[CH:14][C:15]4[C:20]([C:11]3=[N:10][N:9]=2)=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH:5]=[CH:6][CH:7]=1.[CH:21]1[C:33]2[NH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]=2[CH:24]=[CH:23][CH:22]=1.C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.CO.C(Cl)(Cl)Cl.CN1CCCN(C)C1=O>[CH:30]1[C:31]2[N:32]([C:2]3[CH:3]=[C:4]([C:8]4[N:12]5[CH:13]=[CH:14][C:15]6[C:20]([C:11]5=[N:10][N:9]=4)=[CH:19][CH:18]=[CH:17][CH:16]=6)[CH:5]=[CH:6][CH:7]=3)[C:33]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:26]=2[CH:27]=[CH:28][CH:29]=1

Participants

9

Reactant 4

HCID 6854CarbazoleHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 58068469HCID 58068469, compound

Product 1

HCID 58068390HCID 58068390, compoundYield 78%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolventHCID 6212ChloroformSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
180 °C

Procedure

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.

Workup

  1. temperatureAfter the stirring, this mixture was cooled to room temperature
  2. washThe organic layer of the resulting mixture was washed with water
  3. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and saturated brine, and the organic layer was dried over magnesium sulfate
  4. filtrationThe obtained mixture was gravity-filtered
  5. concentrationthe filtrate was concentrated
  6. customto give a solid
  7. customThis solid was purified by silica gel column chromatography (toluene:ethyl acetate=5:1)
  8. customto give a solid
  9. customwas irradiated with ultrasonic waves
  10. filtrationthe solid was collected by suction filtration
  11. customFurther, this solid was recrystallized from toluene, so that the substance which

Sources & evidence

ORD record
ord-d3346602c3144cd48834dcbb48a0b957
Source dataset
uspto-grants-2015_05
Patent number
US09034486B2

Reaction notes

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