Sodium Carbonate → 5-Bromo-2-(4-octylphenyl)pyridine

HRID 2227114Notes

Reaction equation

HRID 2227114 reaction equation
[Br:1][C:2]1[C:3](Br)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:9]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(=O)([O-])[O-].[Na+].[Na+]>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.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:20]2[CH:19]=[CH:18][C:17]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:22][CH:21]=2)=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 8171022,3-DibromopyridineHCID 4197992(4-octylphenyl)boronic Acid

Product 1

HCID 184718205-Bromo-2-(4-octylphenyl)pyridineYield 95%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a 1000 mL round bottom flask equipped with a stirbar was added dibromopyridine 7C (22.506 g), boronic acid 7B (22.356 g), tetrakis(triphenylphosphine)palladium(0) (3.294 g), saturated sodium carbonate solution (238 mL), and toluene (190 mL). A reflux condenser was attached and the reaction was heated at 100° C. for 24 hours. The cooled reaction mixture was extracted with 1:1 hexane:ethyl acetate, and the combined organic layers were washed with brine and dried over magnesium sulfate and the solvent was removed in vacuo. The solid product was dissolved in dichloromethane, placed on silica gel, and silica gel filtered. The elution solvents were hexane, which removed a higher Rf side product, and 2.5% E/H, resulting in 31.251 g of solid. The product was recrystallized from acetonitrile to give 30.125 g of a white solid.

Workup

  1. customTo a 1000 mL round bottom flask equipped with a stirbar
  2. customA reflux condenser was attached
  3. customThe cooled reaction mixture
  4. extractionwas extracted with 1:1 hexane
  5. washethyl acetate, and the combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was removed in vacuo
  8. dissolutionThe solid product was dissolved in dichloromethane
  9. filtrationfiltered
  10. customremoved a higher Rf side product, and 2.5% E/H

Sources & evidence

ORD record
ord-084f9497f27543ada529675940335893
Source dataset
uspto-grants-2002_07
Patent number
US06413448B1

Reaction notes

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