2,6-Dibromopyridine → HCID 23003169, compound

HRID 902043Notes

Reaction equation

HRID 902043 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[C:12]([CH3:19])[CH:11]=1.C(=O)([O-])[O-].[Tl+2]>C1(C)C=CC=CC=1.C(Cl)Cl.CCCCCC.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>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:13]2[CH:14]=[CH:15][C:10]([F:9])=[CH:11][C:12]=2[CH3:19])[N:3]=1

Participants

7

Reactant 3

HCID 122742,6-DibromopyridineHCID 2734665(4-Fluoro-2-methylphenyl)boronic acidHCID 178526101HCID 178526101, compound

Product 1

HCID 23003169HCID 23003169, compoundYield 74.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 21226440Methylenechloride HexaneSolvent

Procedure

In a 100 ml round-bottomed flask, 7.92 g (33.4 mmol) of 2,6-dibromopyridine was dissolved in 50 ml of anhydrous toluene forming a clear, colorless solution. 4-fluoro-2-methylbenzene boronic acid (5.09 g, 33.1 mmol) produced in step A was added forming a white suspension. Thallium carbonate (17.45 g, 37.2 mmol) was added followed by a catalytic amount (150 mg) of Pd(PPh3)4. The mixture was heated to reflux overnight, cooled, and filtered over a pad of silica gel. The silica was washed with CH2Cl2 and the filtrate was evaporated to afford a white solid. The solid was dissolved in a minimal amount of 50% CH2Cl2/hexane and chromatographed on a short column of silica gel using 30% CH2Cl2/hexane to afford 6.55 g (74%) of the 2-bromo-6-(4-fluoro-2-methylphenyl)pyridine as a white solid.

Workup

  1. customforming a white suspension
  2. temperatureThe mixture was heated
  3. temperatureto reflux overnight
  4. temperaturecooled
  5. filtrationfiltered over a pad of silica gel
  6. washThe silica was washed with CH2Cl2
  7. customthe filtrate was evaporated
  8. customto afford a white solid
  9. customchromatographed on a short column of silica gel using 30% CH2Cl2/hexane

Sources & evidence

ORD record
ord-04927e37bf16490583eb07b80b20ef08
Source dataset
uspto-grants-2008_04
Patent number
US07365072B2

Reaction notes

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