Potassium Carbonate → HCID 89568606, compound

HRID 1773063Notes

Reaction equation

HRID 1773063 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[C:15]2[CH:16]=[C:17](Cl)[CH:18]=[C:19]([C:21]4[N:26]=[C:25]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[CH:24]=[C:23]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[N:22]=4)[CH:20]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[N:40]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=[CH:42][C:41]=1[C:50]1[CH:55]=[CH:54][C:53](B(O)O)=[CH:52][CH:51]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(O)CCC.C1(C)C=CC=CC=1>[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[C:15]2[CH:20]=[C:19]([C:21]4[N:26]=[C:25]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[CH:24]=[C:23]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[N:22]=4)[CH:18]=[C:17]([C:53]4[CH:52]=[CH:51][C:50]([C:41]5[CH:42]=[CH:43][C:44]6[C:49](=[CH:48][CH:47]=[CH:46][CH:45]=6)[N:40]=5)=[CH:55][CH:54]=4)[CH:16]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 71039292HCID 71039292, compoundHCID 89568605HCID 89568605, compound

Product 1

HCID 89568606HCID 89568606, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 2631-ButanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

In a stream of argon, 517 mg (0.996 mmol) of 2-[5-(anthracen-9-yl)-3-chlorophenyl]-4,6-diphenylpyrimidine, 299 mg (1.20 mmol) of 4-(quinolin-2-yl)phenylboronic acid and 4.5 mg (20 μmol) of palladium acetate and 29.6 mg (60 μmol) of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl were suspended in a toluene (4.5 mL)/n-butanol (0.5 mL) mixed solvent, and the suspension was heated to 95° C. 800 μL (2.40 mmol) of an aqueous 3.0M potassium carbonate solution was gradually dropwise added to the mixture, and the mixture was stirred at that temperature for 2 hours. Then the reaction mixture was left to be cooled to room temperature, and water was added to the reaction mixture. Then the deposited solid was collected by filtration to give 645 mg of target 2-[5-(anthracen-9-yl)-4′-(quinoline-2-yl) biphenyl-3-yl]-4,6-diphenylpyrimidine as a white solid (yield, 94%).

Workup

  1. additionmixed solvent
  2. waitThen the reaction mixture was left
  3. temperatureto be cooled to room temperature
  4. filtrationThen the deposited solid was collected by filtration
  5. customto give

Sources & evidence

ORD record
ord-4874cf75710c4b4baa5d767d06eba6e6
Source dataset
uspto-grants-2016_02
Patent number
US09252368B2

Reaction notes

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