Potassium Carbonate → 2-[3'-(Dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline

HRID 1751328Notes

Reaction equation

HRID 1751328 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[N:16][C:15]3[C:10](=[C:11]4[CH:25]=[CH:24][CH:23]=[CH:22][C:12]4=[C:13]4[CH:21]=[CH:20][CH:19]=[CH:18][C:14]4=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH:26]1[C:34]2[C:33]3[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=3[S:31][C:30]=2[C:29]([C:39]2[CH:40]=[C:41](B(O)O)[CH:42]=[CH:43][CH:44]=2)=[CH:28][CH:27]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)C.C1(C)C=CC=CC=1>[CH:26]1[C:34]2[C:33]3[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=3[S:31][C:30]=2[C:29]([C:39]2[CH:40]=[C:41]([C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([C:8]4[CH:17]=[N:16][C:15]5[C:10](=[C:11]6[CH:25]=[CH:24][CH:23]=[CH:22][C:12]6=[C:13]6[CH:21]=[CH:20][CH:19]=[CH:18][C:14]6=5)[N:9]=4)[CH:3]=3)[CH:42]=[CH:43][CH:44]=2)=[CH:28][CH:27]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 58261920(3-(Dibenzo[b,d]thiophen-4-yl)phenyl)boronic acidHCID 867038242-(3-Bromophenyl)dibenzo[f,h]quinoxaline

Product 1

HCID 584099982-[3'-(Dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxalineYield 71%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

In a 200 mL three-neck flask were put 3.0 g (7.8 mmol) of 2-(3-bromophenyl)dibenzo[f,h]quinoxaline, 2.6 g (8.6 mmol) of 3-(dibenzothiophen-4-yl)phenylboronic acid obtained in Step 2, 0.24 g (0.78 mmol) of tri(ortho-tolyl)phosphine (P(o-tolyl)3), 78 mL of toluene, 7.8 mL of ethanol, and 12 mL of 2.0 M potassium carbonate aqueous solution. The mixture was degassed by being stirred under reduced pressure, and the air in the flask was replaced with nitrogen. To the mixture was added 35 mg (0.16 mmol) of palladium(II) acetate. The mixture was stirred at 80° C. under a nitrogen stream for 8 hours. After a predetermined period of time had elapsed, the precipitated solid was separated by filtration to give a yellow solid. The solid was washed with water and ethanol, toluene was added thereto, and the resulting mixture was stirred while being heated. The toluene solution was suction-filtered to give 3.1 g of 2-[3′-(dibenzothiophen-4-yl)biphenyl-3-yl]dibenzo[f,h]quinoxaline (abbreviation: 2mDBTBPDBq-II) as a yellow solid (yellow powder) in a yield of 71%.

Workup

  1. customIn a 200 mL three-neck flask were put
  2. customThe mixture was degassed
  3. stirringThe mixture was stirred at 80° C. under a nitrogen stream for 8 hours
  4. waitAfter a predetermined period of time had elapsed
  5. customthe precipitated solid was separated by filtration
  6. customto give a yellow solid
  7. washThe solid was washed with water and ethanol, toluene
  8. additionwas added
  9. stirringthe resulting mixture was stirred
  10. temperaturewhile being heated
  11. filtrationThe toluene solution was suction-filtered

Sources & evidence

ORD record
ord-1fceea9cbcaf44b284fc66f0360e925a
Source dataset
uspto-grants-2015_10
Patent number
US09159934B2

Reaction notes

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