Toluene → 3-(Anthracen-9-yl)pyridine

HRID 535238

Reaction equation

HRID 535238 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2B(O)O)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.Br[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C>[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 122863-BromopyridineHCID 155102139-Anthraceneboronic Acid

Product 1

HCID 2643883-(Anthracen-9-yl)pyridine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

In a 200 mL three-neck flask, 5.2 g (23 mmol) of 9-anthrylboronic acid, 4.0 g (25 mmol) of 3-bromopyridine, 5.2 g (50 mmol) of sodium carbonate, 50 mL of toluene, 25 μL of ethanol, and 25 mL of water were placed. The mixture was degassed by being stirred under reduced pressure, and the air in the flask was replaced with nitrogen. To the mixture, 0.28 g (0.25 mmol) of tetrakis(triphenylphosphine)palladium(0) was added, and the mixture was stirred under nitrogen stream at 80° C. for 7 hours. After a certain period, water was added to the mixture, and an aqueous layer was extracted with toluene. The obtained extracted solution and the organic layer were combined, washed with saturated saline, and dried with magnesium sulfate. The obtained mixture was gravity filtered, and the filtrate was condensed to give an oily substance. The oily substance was recrystallized with toluene/hexane, so that 2.8 g of target yellow powder was obtained in a yield of 46%.

Workup

  1. customThe mixture was degassed
  2. stirringthe mixture was stirred under nitrogen stream at 80° C. for 7 hours
  3. waitAfter a certain period
  4. extractionan aqueous layer was extracted with toluene
  5. extractionThe obtained extracted solution
  6. washwashed with saturated saline
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. customcondensed
  10. customto give an oily substance
  11. customThe oily substance was recrystallized with toluene/hexane, so that 2.8 g of target yellow powder
  12. customwas obtained in a yield of 46%

Sources & evidence

ORD record
ord-dd4688f4826642aca41ac290afdcfd0a
Source dataset
uspto-grants-2014_10
Patent number
US08859108B2

Linked notes

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