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Ethanol → 2-[3,5-bis(9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxaline

HRID 1053999
Notes
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Reaction equation

HRID 1053999 reaction equation
Cl[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[C:5]3[CH:19]=[CH:18][CH:17]=[CH:16][C:6]3=[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]3=2)[N:3]=1.[CH:20]1[C:32]2[N:31]([C:33]3[CH:34]=[C:35](B(O)O)[CH:36]=[C:37]([N:39]4[C:51]5[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=5[C:45]5[C:40]4=[CH:41][CH:42]=[CH:43][CH:44]=5)[CH:38]=3)[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]=2[CH:23]=[CH:22][CH:21]=1.C(O)C.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:20]1[C:32]2[N:31]([C:33]3[CH:34]=[C:35]([C:2]4[CH:11]=[N:10][C:9]5[C:4](=[C:5]6[CH:19]=[CH:18][CH:17]=[CH:16][C:6]6=[C:7]6[CH:15]=[CH:14][CH:13]=[CH:12][C:8]6=5)[N:3]=4)[CH:36]=[C:37]([N:39]4[C:40]5[CH:41]=[CH:42][CH:43]=[CH:44][C:45]=5[C:46]5[C:51]4=[CH:50][CH:49]=[CH:48][CH:47]=5)[CH:38]=3)[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]=2[CH:23]=[CH:22][CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 702Ethanol2×HCID 11430Potassium CarbonateHCID 580194962-Chlorodibenzo[f,h]quinoxalineHCID 59552792(3,5-Di(9H-carbazol-9-yl)phenyl)boronic acid

Product 1

HCID 866802682-[3,5-bis(9H-carbazol-9-yl)phenyl]dibenzo[f,h]quinoxalineYield 94%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Procedure

Into a 100-mL three-neck flask were put 1.2 g (4.8 mmol) of 2-chlorodibenzo[f,h]quinoxaline, 2.1 g (4.7 mmol) of 3,5-bis(9H-carbazol-9-yl)phenylboronic acid, and the air in the flask was replaced with nitrogen. To this mixture were added 18 mL of toluene, 6.0 mL of ethanol, and 6.0 mL of an aqueous solution of potassium carbonate (2.0 mol/L). This mixture was stirred to be degassed while the pressure was reduced. To this mixture was added 0.11 g (0.096 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at 80° C. for six hours under a nitrogen stream, so that a solid was precipitated. The precipitated solid was collected by suction filtration. To the obtained solid was added about 100 mL of water, washed by ultrasonic wave irradiation, and subjected to suction filtration to obtain a solid. To the obtained solid was added about 100 mL of ethanol, washed by ultrasonic wave irradiation, and subjected to suction filtration to obtain a solid. The obtained solid was dissolved in about 1.5 L of hot toluene, and this solution was suction-filtered through Celite and Florisil. A solid obtained by concentration of the filtrate was washed with toluene, so that 2.8 g of a yellow solid, which was the object of the synthesis, was obtained in a yield of 94%. The synthesis scheme of Step 3 is shown in (a-3).

Workup

  1. customInto a 100-mL three-neck flask were put
  2. customto be degassed while the pressure
  3. stirringthe mixture was stirred at 80° C. for six hours under a nitrogen stream
  4. customso that a solid was precipitated
  5. filtrationThe precipitated solid was collected by suction filtration
  6. additionTo the obtained solid was added about 100 mL of water
  7. washwashed by ultrasonic wave irradiation
  8. filtrationsubjected to suction filtration
  9. customto obtain a solid
  10. washwashed by ultrasonic wave irradiation
  11. filtrationsubjected to suction filtration
  12. customto obtain a solid
  13. filtrationthis solution was suction-filtered through Celite and Florisil
  14. customA solid obtained by concentration of the filtrate
  15. washwas washed with toluene, so that 2.8 g of a yellow solid, which
  16. customthe object of the synthesis
  17. customwas obtained in a yield of 94%
  18. customThe synthesis scheme of Step 3

Sources & evidence

ORD record
ord-6eee3540a6754423b107bbb9acf9f813
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09394280B2

Reaction notes

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