Potassium Carbonate → HCID 57772934, compound

HRID 1910371Notes

Reaction equation

HRID 1910371 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:14]([C:15]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[C:16]4[C:21]=2[CH:20]=[CH:19][CH:18]=[CH:17]4)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:4][CH:3]=1.[C:28]1([N:34]2[C:46]3[CH:45]=[CH:44][C:43](B(O)O)=[CH:42][C:41]=3[C:40]3[C:35]2=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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>[C:28]1([N:34]2[C:46]3[CH:45]=[CH:44][C:43]([C:2]4[CH:3]=[CH:4][C:5]([C:8]5[C:21]6[C:16]([C:15]([C:22]7[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=7)=[C:14]7[C:9]=5[CH:10]=[CH:11][CH:12]=[CH:13]7)=[CH:17][CH:18]=[CH:19][CH:20]=6)=[CH:6][CH:7]=4)=[CH:42][C:41]=3[C:40]3[C:35]2=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 221382759-(4-Bromophenyl)-10-phenylanthraceneHCID 513584509-Phenyl-9H-carbazole-3-boronic acid

Product 1

HCID 57772934HCID 57772934, compoundYield 75%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
90 °C

Procedure

In a 200 mL three-neck flask were stirred 1.9 g (4.7 mmol) of 9-(4-Bromophenyl)-10-phenylanthracene (abbreviation: PA) obtained by the above Steps 1(1) to 1(4) described in Synthesis Example 1, 1.4 g (4.7 mmol) of 9-phenyl-9H-carbazol-3-boronic acid obtained by the above Step 1 described in Synthesis Example 2, 5.6 mg (25 μmol) of Palladium(II) acetate (abbreviation: Pd(OAc)2), 52 mg (170 μmol) of tris(o-tolyl)phosphine (abbreviation: P(o-tolyl)3), 7 mL (15 mmol) of potassium carbonate aqueous solution (2.0 mol/L), and 40 mL of 1,2-dimethoxyethane (abbreviation: DME) in a nitrogen atmosphere for 7 hours while being heated at 90° C. After that, the temperature of this suspending solution was cooled to room temperature, and the mixture was filtered to provide a residue. The obtained residue was dissolved into 50 mL of hot toluene, and the mixture was filtered through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), alumina, and celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855) while 400 mL of toluene was added. The obtained filtrate was condensed, hexane was added therein, ultrasonic waves were applied thereto, and then recrystallization thereof was performed. Accordingly, 2.0 g of a powdery light-yellow solid of 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol (abbreviation: PCzPA), which was the object of the synthesis, was obtained in a yield of 75% (synthesis scheme (b-2)).

Workup

  1. customobtained by the above Steps 1(1) to 1(4)
  2. customobtained by the above Step 1
  3. temperatureAfter that, the temperature of this suspending solution was cooled to room temperature
  4. filtrationthe mixture was filtered
  5. customto provide a residue
  6. filtrationthe mixture was filtered through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), alumina, and celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855) while 400 mL of toluene
  7. additionwas added
  8. customcondensed, hexane
  9. additionwas added
  10. customrecrystallization
  11. customthe object of the synthesis
  12. customwas obtained in a yield of 75% (synthesis scheme (b-2))

Sources & evidence

ORD record
ord-9d082e88122942698222a2ff7e461bce
Source dataset
uspto-grants-2013_12
Patent number
US08603644B2

Reaction notes

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