Toluene → 2-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinoline

HRID 626603Notes

Reaction equation

HRID 626603 reaction equation
Cl[C:2]1[CH:11]=[CH: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:28]2[C:27]3[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=3[S:25][C:24]=2[C:23]([C:33]2[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=2)=[CH:22][CH:21]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>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.CO.O.C(O)C>[CH:20]1[C:28]2[C:27]3[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=3[S:25][C:24]=2[C:23]([C:33]2[CH:34]=[C:35]([C:2]3[CH:11]=[CH:10][C:9]4[C:4](=[C:5]5[CH:19]=[CH:18][CH:17]=[CH:16][C:6]5=[C:7]5[CH:15]=[CH:14][CH:13]=[CH:12][C:8]5=4)[N:3]=3)[CH:36]=[CH:37][CH:38]=2)=[CH:22][CH:21]=1

Participants

9

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 58261920(3-(Dibenzo[b,d]thiophen-4-yl)phenyl)boronic acidHCID 866755612-Chlorodibenzo[f,h]quinoline

Product 1

HCID 866755602-[3-(Dibenzothiophen-4-yl)phenyl]dibenzo[f,h]quinolineYield 82%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In a 100-mL three-neck flask, 0.46 g (1.7 mmol) of 2-chlorodibenzo[f,h]quinoline, 0.62 g (2.0 mmol) of 3-(dibenzothiophen-4-yl)phenylboronic acid, 20 mL of toluene, 2 mL of ethanol, and 2 mL of a 2M aqueous solution of potassium carbonate were put. The mixture was degassed by being stirred under reduced pressure, and the air in the flask was replaced with nitrogen. To the mixture, 65 mg (56 μmol) of tetrakis(triphenylphosphine)palladium(0) was added, and the mixture was stirred under nitrogen stream at 80° C. for 7 hours. After a predetermined time, water was added to the mixture, and an aqueous layer was extracted with toluene. The obtained extract combined with the organic layer was washed with a saturated aqueous solution of sodium carbonate and a saturated solution of sodium chloride, and the resulting organic layer was dried with magnesium sulfate. The obtained mixture was gravity filtered, and the filtrate was condensed to give an oily substance. The obtained oily substance was purified by silica gel column chromatography (toluene:hexane=1:1), so that a solid was obtained. The solid was purified by high performance liquid column chromatography. The high performance liquid column chromatography was performed using chloroform as a developing solvent. The obtained fraction was condensed to obtain a solid. A methanol suspension of the obtained solid was irradiated with ultrasonic waves, and a solid was collected by suction filtration, so that the objective substance was obtained as 0.68 g of white powder in 79% yield.

Workup

  1. customThe mixture was degassed
  2. stirringthe mixture was stirred under nitrogen stream at 80° C. for 7 hours
  3. extractionan aqueous layer was extracted with toluene
  4. extractionThe obtained extract
  5. washwas washed with a saturated aqueous solution of sodium carbonate
  6. dry with materiala saturated solution of sodium chloride, and the resulting organic layer was dried with magnesium sulfate
  7. filtrationfiltered
  8. customcondensed
  9. customto give an oily substance
  10. customThe obtained oily substance was purified by silica gel column chromatography (toluene:hexane=1:1), so that a solid
  11. customwas obtained
  12. customThe solid was purified by high performance liquid column chromatography
  13. customcondensed
  14. customto obtain a solid
  15. customwas irradiated with ultrasonic waves
  16. filtrationa solid was collected by suction filtration, so that the objective substance

Sources & evidence

ORD record
ord-adc06a3cdcbe4919944a91149a8b7b84
Source dataset
uspto-grants-2016_04
Patent number
US09309223B2

Reaction notes

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