Sodium Carbonate → 3-(2-Thienyl)pyridine

HRID 1636789

Reaktionsgleichung

Reaktionsgleichung von HRID 1636789
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

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 122863-BromopyridineHCID 27339602-Thiopheneboronic acid

Produkt 1

HCID 5951453-(2-Thienyl)pyridineAusbeute 16,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-bromopryidine (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 minutes. 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 filtrate 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.

Aufarbeitung

  1. temperaturethe resulting mixture is refluxed overnight
  2. temperatureThe solution is cooled to room temperature
  3. filtrationfiltered through Celite
  4. extractionThe filtrate 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

Quellen und Nachweise

ORD-Eintrag
ord-53f861b5fa314b8c908bcd6e8c7a98b2
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06034093

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