Sodium Carbonate → HCID 21964083, compound

HRID 2212135Notes

Reaction equation

HRID 2212135 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[O:9]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.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.O.C(O)C.C1(C)C=CC=CC=1>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:7]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 693693,5-DibromopyridineHCID 27343774-Phenoxyphenylboronic acid

Product 1

HCID 21964083HCID 21964083, compoundYield 32.3%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, a mixture of 3,5-dibromopyridine (5.16 g, 21.8 mmol), water (36.5 mL), toluene (145 mL), ethanol (36.5 mL), 4-phenoxyphenylboronic acid (5.00 g, 23.3 mmol), sodium carbonate (4.9 g, 47 mmol) and tetrakis(triphenylphosphine)palladium (1.25 g, 1.04 mmol) was stirred and heated under reflux for 5 h. After cooling to room temperature, water (150 mL) was added and the aqueous phase separated and extracted with ethyl acetate (3×100 mL). The combined organic phases were washed with water (50 mL), then dried (MgSO4), treated with 3S Black (decolorizing charcoal), filtered, and concentrated by rotary evaporation. The residue was purified by column chromatography, eluting with cyclohexane/ethyl acetate (90/10, v/v) to give 2.3 g (32%) of a white solid, mp 109° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 h
  3. customthe aqueous phase separated
  4. extractionextracted with ethyl acetate (3×100 mL)
  5. washThe combined organic phases were washed with water (50 mL)
  6. dry with materialdried (MgSO4)
  7. additiontreated with 3S Black (decolorizing charcoal)
  8. filtrationfiltered
  9. concentrationconcentrated by rotary evaporation
  10. customThe residue was purified by column chromatography
  11. washeluting with cyclohexane/ethyl acetate (90/10

Sources & evidence

ORD record
ord-1f27415001764f7faee5a1a96b245ec1
Source dataset
uspto-grants-2006_09
Patent number
US07101896B2

Reaction notes

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