Potassium Carbonate → HCID 57668727, compound

HRID 1910338Notes

Reaction equation

HRID 1910338 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[Br:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O.COCCOC>[Br:9][C:10]1[CH:15]=[C:14]([C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=2)[CH:13]=[CH:12][CH:11]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 5642162-Bromo-5-methylpyridineHCID 2734318(3-Bromophenyl)boronic acid

Product 1

HCID 57668727HCID 57668727, compoundYield 68.1%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-5-methylpyridine (46.1 g, 267 mmol), 3-bromophenylboronic acid (35.8 g, 178 mmol), palladium(II) acetate (1.00 g, 4.4 mmol), triphenylphosphine (4.67 g, 17.8 mmol), and potassium carbonate (67.8 g, 491 mmol) were mixed with 370 mL of ethylene glycol dimethyl ether and 245 mL of water in a 1000 mL round bottom flask equipped with a temperature probe, reflux condenser, and a magnetic stir bar. The solution was heated at reflux under nitrogen for 16 hr. The cooled reaction mixture was then placed in a separatory funnel, and 100 mL of ethyl acetate was added. The aqueous layer was discarded. The organic layer was extracted twice with a saturated solution of sodium chloride, dried over magnesium sulfate, and evaporated to dryness. After the excess 2-bromo-5-methylpyridine was distilled off in vacuo at 110° C., the 2-(3-bromophenyl)-5-methylpyridine was distilled at 200° C. to give 30.1 g (68.1% yield) of a slightly orange liquid, which was used for the next step without further purification.

Workup

  1. customequipped with a temperature probe
  2. temperaturereflux condenser, and a magnetic stir bar
  3. temperatureThe solution was heated
  4. temperatureat reflux under nitrogen for 16 hr
  5. customThe cooled reaction mixture
  6. customwas then placed in a separatory funnel
  7. extractionThe organic layer was extracted twice with a saturated solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. customevaporated to dryness
  10. distillationAfter the excess 2-bromo-5-methylpyridine was distilled off in vacuo at 110° C.
  11. distillationthe 2-(3-bromophenyl)-5-methylpyridine was distilled at 200° C.
  12. customto give 30.1 g (68.1% yield) of a slightly orange liquid, which
  13. customwas used for the next step without further purification

Sources & evidence

ORD record
ord-56e2cb674b804a07baecd1f5a53c69e6
Source dataset
uspto-grants-2013_12
Patent number
US08603645B2

Reaction notes

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