Potassium Carbonate → 12,12-Dimethyl-10-phenyl-7-(4-diphenylamino-phenyl)-10,12-dihydroindeno[2,1-b]carbazole

HRID 719048Notes

Reaction equation

HRID 719048 reaction equation
Br[C:2]1[C:10]2[CH:11]=[C:12]3[C:20]([C:21]([CH3:23])([CH3:22])[C:9]=2[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:7]=2)=[C:19]1[C:14]([CH:15]=[CH:16][CH:17]=[CH:18]1)=[N:13]3.[C:30]1([N:36]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:37]2[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1(C)C=CC=CC=1.C(O)C.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.O.C1(C)C=CC=CC=1>[CH3:22][C:21]1([CH3:23])[C:20]2[C:12]([N:13]=[C:14]3[C:19]=2[CH:18]=[CH:17][CH:16]=[CH:15]3)=[CH:11][C:10]2[C:2]([C:40]3[CH:41]=[CH:42][C:37]([N:36]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)=[CH:38][CH:39]=3)=[C:3]3[C:8]([C:9]1=2)=[CH:7][CH:6]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:5]=[CH:4]3

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 121669344-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride)HCID 21863594Toluene ethanolHCID 866850157-Bromo-12,12-dimethyl-10-phenyl-10,12-dihydroindeno[2,1-b]carbazole

Product 1

HCID 8957261812,12-Dimethyl-10-phenyl-7-(4-diphenylamino-phenyl)-10,12-dihydroindeno[2,1-b]carbazoleYield 58.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
73 °C

Procedure

7-Bromo-12,12-dimethyl-10-phenyl-10,12-dihydroindeno[2,1-b]carbazole synthesized in Example 1 (2.0 g), 4-diphenylamino-phenylboronic acid (1.32 g), a toluene/ethanol (4/1, v/v) mixed solvent (15 ml), and a 2M potassium carbonate aqueous solution (3.4 ml) were added to a nitrogen-substituted reaction vessel and aerated with nitrogen gas for 30 min under ultrasonic irradiation. The mixture was heated after adding tetrakis(triphenylphosphine)palladium (0.26 g), and stirred at 73° C. for 5 hours. After the mixture was cooled to a room temperature, toluene (30 ml) and water (20 ml) were added to perform liquid separation in order to collect an organic layer. The organic layer was washed with saturated brine, dehydrated with anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (carrier: silica gel; eluent: toluene/n-hexane) to obtain a pale yellowish white powder of 12,12-dimethyl-10-phenyl-7-(4-diphenylamino-phenyl)-10,12-dihydroindeno[2,1-b]carbazole (1.6 g; yield 58.4%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureAfter the mixture was cooled to a room temperature
  3. customliquid separation in order
  4. customto collect an organic layer
  5. washThe organic layer was washed with saturated brine
  6. concentrationconcentrated under reduced pressure
  7. customto obtain a crude product
  8. customThe crude product was purified by column chromatography (carrier: silica gel; eluent: toluene/n-hexane)

Sources & evidence

ORD record
ord-9ce390a62436465cb048a628dc408cbe
Source dataset
uspto-grants-2015_11
Patent number
US09196837B2

Reaction notes

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