Sodium Carbonate → 4-(4-Isopropylphenyl)pyridine

HRID 628832Notes

Reaction equation

HRID 628832 reaction equation
Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=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+]>C(#N)C.O>[CH:9]([C:12]1[CH:17]=[CH:16][C:15]([C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)=[CH:14][CH:13]=1)([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 881004-Bromopyridinium chlorideHCID 27734804-Isopropylphenylboronic acid

Product 1

HCID 229510894-(4-Isopropylphenyl)pyridine

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Part A. A solution of 4-bromopyridine hydrochloride (1.0 g, 6.3 mmol) in acetonitrile-water (50 mL/20 mL) is treated with 4-isopropylbenzeneboronic acid (1.04 g, 6.3 mmol) and sodium carbonate (2.1 g, 25.2 mmol). The mixture is degassed twice, and a catalytic quantity of tetrakis(triphenylphosphine)palladium is added. The mixture is heated to reflux for 12 h., then cooled and poured into water (50 mL). The mixture is filtered and extracted with ethyl acetate (3×50 mL). The extracts are combined, washed with brine, dried over magnesium sulfate, filtered and evaporated to afford 1.01 g of sufficiently pure product, 4-(4-isopropyl-phenyl)-pyridine.

Workup

  1. customThe mixture is degassed twice
  2. additiona catalytic quantity of tetrakis(triphenylphosphine)palladium is added
  3. temperatureThe mixture is heated
  4. temperatureto reflux for 12 h.
  5. temperaturecooled
  6. additionpoured into water (50 mL)
  7. filtrationThe mixture is filtered
  8. extractionextracted with ethyl acetate (3×50 mL)
  9. washwashed with brine
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-9ccb15b898d346b8b3265b38e81e11f7
Source dataset
uspto-grants-2016_04
Patent number
US09315467B2

Reaction notes

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