Toluene → HCID 57879970, compound

HRID 1816864Notes

Reaction equation

HRID 1816864 reaction equation
[C:1]1([C:7]2[N:8]([C:16]3[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=3)[C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:26]1[CH:31]=[CH:30][C:29]([N:32]2[C:44]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[C:38]3[C:33]2=[CH:34][CH:35]=[CH:36][CH:37]=3)=[CH:28][CH:27]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C>[C:1]1([C:7]2[N:8]([C:16]3[CH:21]=[CH:20][C:19]([C:26]4[CH:31]=[CH:30][C:29]([N:32]5[C:33]6[CH:34]=[CH:35][CH:36]=[CH:37][C:38]=6[C:39]6[C:44]5=[CH:43][CH:42]=[CH:41][CH:40]=6)=[CH:28][CH:27]=4)=[CH:18][CH:17]=3)[C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 223613909-(4-Bromophenyl)carbazoleHCID 57879964HCID 57879964, compound

Product 1

HCID 57879970HCID 57879970, compoundYield 38.6%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolvent

Procedure

0.78 g (2.49 mmole) of 4-(2-phenylindole-1-yl)phenyl boronic acid and 0.80 g (2.48 mmole) of 9-(4-bromophenyl)carbazole were put in a 20 ml three-necked flask, and 2.5 ml of toluene, 1.5 ml of ethanol, and 2.5 ml of 2M-sodium carbonate solution were put therein, and 0.09 g (0.08 mmole) of tetrakis-(triphenylphosphine) palladium (0) was added under stirring at room temperature under nitrogen flow. Then, the mixture was refluxed with stirring for 5 hours under nitrogen flow. After the reaction was completed, the reaction mixture was cooled to room temperature and deposited crystal was separated by filtration. The crystal was washed with acetone and recrystallized with a mixed solvent of toluene/ethanol. The obtained crystal was refined by alumina column chromatography (eluent:toluene) and crystallize with methanol to give 0.49 g of a white crystal of 4-(2-phenylindole-1-yl)-4′-(carbazole-9-yl)biphenyl (Exemplary Compound No. 34)(yield: 38.6%).

Workup

  1. temperatureThen, the mixture was refluxed
  2. stirringwith stirring for 5 hours under nitrogen flow
  3. temperaturethe reaction mixture was cooled to room temperature
  4. customwas separated by filtration
  5. washThe crystal was washed with acetone
  6. customrecrystallized with a mixed solvent of toluene/ethanol
  7. customcrystallize with methanol

Sources & evidence

ORD record
ord-3f88218d47d6417394016e6ff5599050
Source dataset
uspto-grants-2009_10
Patent number
US07597955B2

Reaction notes

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