Sodium Carbonate → HCID 69234639, compound

HRID 628837Notes

Reaction equation

HRID 628837 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[CH:9]([C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1)([CH3:11])[CH3:10].C(=O)([O-])[O-].[Na+].[Na+]>>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:15]2[CH:16]=[CH:17][C:12]([CH:9]([CH3:11])[CH3:10])=[CH:13][CH:14]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 693693,5-DibromopyridineHCID 27734804-Isopropylphenylboronic acid

Product 1

HCID 69234639HCID 69234639, compoundYield 55%

Conditions

Temperature
80 °C

Procedure

Part A. A solution of 3,5-dibromopyridine (1.0 g, 4.2 mmol) and 4-isopropylbenzeneboronic acid (346 mg, 2.1 mmol) in a mixture of ethanol-toluene-water (10 mL/5 mL/3 mL) is treated with sodium carbonate (450 mg). The mixture is degassed twice, treated with a catalytic amount of tetrakis(triphenylphosphine)palladium, and heated with stirring to 80° C. for 12 h. The mixture is cooled, filtered and evaporated. The residue is partitioned between water and ethyl acetate, and the organic phase is washed with brine, dried over sodium sulfate, filtered and evaporated. The residue is separated by column chromatography to afford 3-bromo-5-(4-isopropyl-phenyl)-pyridine (300 mg, 55%).

Workup

  1. customThe mixture is degassed twice
  2. additiontreated with a catalytic amount of tetrakis(triphenylphosphine)palladium
  3. temperatureheated
  4. temperatureThe mixture is cooled
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is partitioned between water and ethyl acetate
  8. washthe organic phase is washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue is separated by column chromatography

Sources & evidence

ORD record
ord-7b89103cd64b467a8d7991b2f150d9f6
Source dataset
uspto-grants-2016_04
Patent number
US09315467B2

Reaction notes

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