Sodium Carbonate → 3-(2-Thienyl)pyridine

HRID 2771

Reaction equation

HRID 2771 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 122863-BromopyridineHCID 27339602-Thiopheneboronic acid

Product 1

HCID 5951453-(2-Thienyl)pyridineYield 16.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 3-bromopyridine (1.30 mL, 13.5 mmol) and tetrakis(triphenylphosphine) (0.468 g, 0.41 mmol) in 40 mL of dimethoxyethane is stirred under nitrogen at room temperature for 10 min. 2-Thiophene boronic acid (1.90 g, 14.8 mmol) and 20 mL of 1N sodium carbonate are added and the resulting mixture is refluxed overnight. The solution is cooled to room temperature and filtered through Celite. The filtrated is extracted with ether (2×30 mL). The combined organic layers are dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with a gradient of 10% EtOAc/hexanes to 20% EtOAc/hexanes to afford the title compound (0.355 g, 2.20 mmol) as a light yellow oil.

Workup

  1. temperaturethe resulting mixture is refluxed overnight
  2. temperatureThe solution is cooled to room temperature
  3. filtrationfiltered through Celite
  4. extractionThe filtrated is extracted with ether (2×30 mL)
  5. dry with materialThe combined organic layers are dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is purified by column chromatography
  9. washeluting with a gradient of 10% EtOAc/hexanes to 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-8d5d986597254a4b95b496e32a884a31
Source dataset
uspto-grants-1998_03
Patent number
US05731315

Linked notes

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