Toluene → 5-Bromo-2-(2-methylphenyl)pyridine

HRID 2220252Notes

Reaction equation

HRID 2220252 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[N:6][CH:7]=1.[C:9]1([CH3:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(=O)([O-])[O-].[Na+].[Na+].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH3:15])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 1140TolueneHCID 5936905-Bromo-2-iodopyridine

Product 1

HCID 131283855-Bromo-2-(2-methylphenyl)pyridineYield 84%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 10340Sodium CarbonateSolvent

Procedure

To an argon-purged and evacuated slurry of 910 mg (3.21 mmol) of 5-bromo-2-iodopyridine and 436 mg (3.21 mmol, 1.0 eq.) of 2-o-tolylboronic acid in 8 mL of toluene and 3.2 mL of 2 M aqueous sodium carbonate, was added 36 mg (0.032 mmol, 0.01 eq) of tetrakis(triphenylphosphine) palladium. The reaction mixture was purged and evacuated with argon twice more and then set to reflux under argon for 15 h. The reaction was cooled and partitioned between water and EtOAc. The layers were separated, and the aqueous layer extracted once more with EtOAc. The organic extracts were combined, dried over magnesium sulfate, filtered, concentrated and dried in vacuo to give the crude product as an orange oil. Purification by silica gel chromatography (7:3 CH2Cl2/hexanes) provided the title compound as a yellow oil, 666 mg, 84% yield.

Workup

  1. customTo an argon-purged
  2. customThe reaction mixture was purged
  3. customevacuated with argon twice more
  4. temperatureto reflux under argon for 15 h
  5. temperatureThe reaction was cooled
  6. custompartitioned between water and EtOAc
  7. customThe layers were separated
  8. extractionthe aqueous layer extracted once more with EtOAc
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customdried in vacuo
  13. customto give the crude product as an orange oil
  14. customPurification by silica gel chromatography (7:3 CH2Cl2/hexanes)

Sources & evidence

ORD record
ord-11b7b240fac34c139fa4e1a44b7f1622
Source dataset
uspto-grants-2008_08
Patent number
US07417028B2

Reaction notes

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