Potassium Carbonate → 3-[4-(Benzoxazol-2-yl)phenyl]-6,9-diphenyl-9H-carbazole

HRID 1028872Notes

Reaction equation

HRID 1028872 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([C:23]2[CH:24]=[C:25]3[C:33](=[CH:34][CH:35]=2)[N:32]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:31]2[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][C:26]3=2)[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.C(Cl)(Cl)Cl.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:28]2[CH:29]=[CH:30][C:31]3[N:32]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:33]4[C:25]([C:26]=3[CH:27]=2)=[CH:24][C:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:35][CH:34]=4)=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 128467152-(4-Bromophenyl)benzo(d)oxazoleHCID 597285856,9-Diphenyl-9H-carbazole-3-boronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 592280403-[4-(Benzoxazol-2-yl)phenyl]-6,9-diphenyl-9H-carbazole

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6212ChloroformSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

In a 100 mL three-neck flask were put 0.75 g (2.8 mmol) of 2-(4-bromophenyl)benzoxazole, 1.0 g (2.8 mmol) of 6,9-diphenyl-9H-carbazole-3-boronic acid, and 0.060 g (0.20 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 6.2 mg (0.028 mmol) of palladium(II)acetate, and the resulting mixture was stirred at 90° C. for 3 hours while being heated. After that, chloroform 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. After that, this mixture was suction filtered. The resulting filtration was suction filtered through Celite 545 (produced by Kishida Chemical Co., Ltd., Catalog No. 020-14815), 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. temperaturewhile being heated
  4. washthis suspension was washed with a saturated aqueous sodium carbonate solution and saturated brine in that order
  5. additionThen, magnesium sulfate was added to the organic layer
  6. customto dry it
  7. filtrationfiltered
  8. filtrationThe resulting filtration
  9. filtrationfiltered through Celite 545 (produced by Kishida Chemical Co., Ltd., Catalog No. 020-14815), whereby a filtrate
  10. customwas obtained

Sources & evidence

ORD record
ord-9d38a23a9b954daa882a9ae043af7656
Source dataset
uspto-grants-2014_05
Patent number
US08735597B2

Reaction notes

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