Sodium Carbonate → 2-Bromo-6-phenylpyridine

HRID 1796069Notes

Reaction equation

HRID 1796069 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.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:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 122742,6-DibromopyridineHCID 66827Phenylboronic Acid

Product 1

HCID 5686792-Bromo-6-phenylpyridineYield 4.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A degassed solution of 2,6-dibromopyridine (4.0 g, 16.5 mmol) and phenylboronic acid (2.1 g, 16.7 mmol) in dry tetrahydrofuran (30 ml) was stirred under an atmosphere of nitrogen then sodium carbonate (3.55 g, 33.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.95 g, 5 mol %) added. This mixture was heated to reflux for 18 h. After cooling to ambient temperature, solvent was removed in vacuo, the residue dissolved in dichloromethane, washed with water and saturated brine, then dried over magnesium sulfate, filtered and evaporated in vacuo to give a solid. Purification by chromatography on silica gel eluting with dichloromethane gave 2-bromo-6-phenylpyridine (0.17 g) as a white solid: δH (400 MHz, CDCl3) 7.45 (4H, m), 7.60 (1H, dd, J 8 and 8), 7.70 (1H, d, J 8), 7.99 (2H, d, J 8); m/z (ES+) 233/235 (M++H).

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 18 h
  3. customsolvent was removed in vacuo
  4. dissolutionthe residue dissolved in dichloromethane
  5. washwashed with water and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto give a solid
  10. customPurification by chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-5c452eab8b9046feb80c87a1dff4284d
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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