Potassium Carbonate → 3-[4-(Benzoxazol-2-yl)phenyl]-9-phenyl-9H-carbazole

HRID 1028871Notes

Reaction equation

HRID 1028871 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[C:17]1([N:23]2[C:35]3[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][C:30]=3[C:29]3[C:24]2=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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.C1(C)C=CC=CC=1.COCCOC>[O:9]1[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=[C:8]1[C:5]1[CH:6]=[CH:7][C:2]([C:32]2[CH:33]=[CH:34][C:35]3[N:23]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:24]4[C:29]([C:30]=3[CH:31]=2)=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 128467152-(4-Bromophenyl)benzo(d)oxazoleHCID 513584509-Phenyl-9H-carbazole-3-boronic acid

Product 1

HCID 592280513-[4-(Benzoxazol-2-yl)phenyl]-9-phenyl-9H-carbazole

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

In a 100 mL three-neck flask were put 0.95 g (3.5 mmol) of 2-(4-bromophenyl)benzoxazole, 1.0 g (3.5 mmol) of 9-phenyl-9H-carbazole-3-boronic acid, and 0.074 g (0.24 mmol) of tri(ortho-tolyl)phosphine. To this mixture were added 15 mL of 1,2-dimethoxyethane (abbreviation: DME) and 5 mL of a 2M potassium carbonate aqueous solution. This mixture was degassed under reduced pressure, and then the atmosphere in the flask was replaced with nitrogen. To this mixture was added 7.8 mg (0.035 mmol) of palladium(II)acetate, and the resulting mixture was stirred at 100° C. for 5 hours. After that, toluene was added to this mixture, and this suspension was washed with a saturated aqueous sodium carbonate solution and saturated brine in that order. Then, magnesium sulfate was added to the organic layer to dry it. Next, this mixture was suction filtered, whereby a filtrate was obtained.

Workup

  1. customIn a 100 mL three-neck flask were put
  2. customThis mixture was degassed under reduced pressure
  3. washthis suspension was washed with a saturated aqueous sodium carbonate solution and saturated brine in that order
  4. additionThen, magnesium sulfate was added to the organic layer
  5. customto dry it
  6. filtrationfiltered
  7. customwhereby a filtrate was obtained

Sources & evidence

ORD record
ord-f838151a5a0643c1a27a6b4fcc1244e6
Source dataset
uspto-grants-2014_05
Patent number
US08735597B2

Reaction notes

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