Potassium Carbonate → 2-{3-[3-(Dibenzothiophen-4-yl)phenyl]phenyl}dibenzo[f,h]quinoline

HRID 626606Notes

Reaction equation

HRID 626606 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[CH: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.CO.C1(C)C=CC=CC=1.O.C(O)C>[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:3]=[C:4]([C:8]4[CH:17]=[CH: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:5]=[CH:6][CH:7]=3)[CH:42]=[CH:43][CH:44]=2)=[CH:28][CH:27]=1

Participants

10

Reactant 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 58261920(3-(Dibenzo[b,d]thiophen-4-yl)phenyl)boronic acidHCID 866755632-(3-Bromophenyl)dibenzo[f,h]quinoline

Product 1

HCID 866755622-{3-[3-(Dibenzothiophen-4-yl)phenyl]phenyl}dibenzo[f,h]quinolineYield 63%

Reagents, catalysts & solvents 5

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

In a 50-mL three-neck flask, 0.56 g (1.5 mmol) of 2-(3-bromophenyl)dibenzo[f,h]quinoline, 0.46 g (1.5 mmol) of 3-(dibenzothiophen-4-yl)phenylboronic acid, 58 mg (0.19 mmol) of tri(ortho-tolyl)phosphine, 15 mL of toluene, 1.5 mL of ethanol, and 1.5 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. Then, 17 mg (77 μmol) of palladium(II) acetate was added to this mixture, and the mixture was stirred at 80° C. for 9 hours under a nitrogen stream. After a predetermined time, water and toluene were added to this mixture, and the resulting solid was collected by suction filtration. A toluene solution of the obtained solid was suction-filtered through alumina and Celite, and the filtrate was concentrated to give a yellow solid. A methanol suspension of the obtained solid was irradiated with ultrasonic waves, and a solid was collected by suction filtration, so that the object of the synthesis was obtained as 0.52 g of white powder in 63% yield.

Workup

  1. customThe mixture was degassed
  2. stirringthe mixture was stirred at 80° C. for 9 hours under a nitrogen stream
  3. filtrationthe resulting solid was collected by suction filtration
  4. filtrationA toluene solution of the obtained solid was suction-filtered through alumina and Celite
  5. concentrationthe filtrate was concentrated
  6. customto give a yellow solid
  7. customwas irradiated with ultrasonic waves
  8. filtrationa solid was collected by suction filtration, so that the object of the synthesis

Sources & evidence

ORD record
ord-f9033963dc924b349ea16896d18172f4
Source dataset
uspto-grants-2016_04
Patent number
US09309223B2

Reaction notes

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