Sodium Carbonate → HCID 21964083, compound

HRID 2181157Notes

Reaction equation

HRID 2181157 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-0de2978bd3fd48d294ea8b994052b100
Source dataset
uspto-grants-2005_05
Patent number
US06890935B2

Reaction notes

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