Reaktion #809291

Reaktionsgleichung

4-Bromo-2,3,5-trimethyl-pyridine 1-oxide

trimethylaluminum

ammonium chloride

→

2,3,4,5-Tetramethyl-pyridine 1-oxide

Lösungsmittel

THF

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe solution was heated
2. 2
   Temperaturto reflux for 3 h
3. 3
   Sonstigebefore quenching
4. 4
   Sonstigethe reaction with 4 mL of methanol
5. 5
   TemperaturThe mixture was refluxed for 2 h
6. 6
   Filtrationfiltered

Vorschrift

4-Bromo-2,3,5-trimethyl-pyridine 1-oxide (2 g, 9.2 mmole) and catalytic tetrakis(triphenylphosphino)-palladium (80 mg, 4% by wt) in 20 mL of dry THF before treating with trimethylaluminum (2M in toluene, 15.2 mmole) under nitrogen. The solution was heated to reflux for 3 h, diluted with toluene (20 mL) before quenching the reaction with 4 mL of methanol followed by ammonium chloride (15 mmole). The mixture was refluxed for 2 h and filtered, while hot, on Celite. See J. Med. Chem. 1999, 42(12), 2064–2086. HPLC Rt: 4.183 min. 1H-NMR (CDCl3): δ 8.05 (s, 1H), 2.55 (s, 3H), 2.27 (s, 3H), 2.22 (s, 3H), 2.20 (s, 3H).

Quelle