Reaktion #587932

Reaktionsgleichung

water

2-bromo-1-p-tolyl-ethanone

5-methyl-pyridin-2-yl-amine

NaHCO3

→

6-methyl-2-p-tolyl-imidazo[1,2-a]pyridine

Ausbeute 70.4%

Lösungsmittel

dimethylformamide

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 1.5 hours
2. 2
   TemperaturThe mixture was cooled
3. 3
   SonstigeThe solid was collected
4. 4
   Waschenwashed with water (2 mL)
5. 5
   Sonstigerecrystallized from dimethylformamide (5 mL)

Vorschrift

A solution of 2-bromo-1-p-tolyl-ethanone (500 mg, 2.3 mmol) in dimethylformamide (2 mL) was added slowly to a solution of 5-methyl-pyridin-2-yl-amine (249 mg, 2.3 mmol) in dimethylformamide (2 mL). NaHCO3 (386 mg, 4.6 mmol) was added in portions and the mixture was stirred at room temperature for 15 minutes, then at reflux for 1.5 hours. The mixture was cooled and poured into water (5 mL). The solid was collected, washed with water (2 mL) and recrystallized from dimethylformamide (5 mL) to yield the desired product 6-methyl-2-p-tolyl-imidazo[1,2-a]pyridine (360 mg, 70%). 1H NMR (300 MHz, DMSO-d6) δ 2.27 (s, 3H), 2.32 (s, 3H), 7.08 (d, 1H), 7.21 (d, 2H), 7.46 (d, 1H), 7.83 (d, 2H), 8.24 (s, 1H), 8.29 (s, 1H); ESI-MS (MH+), 223.

Quelle