Triethyl orthoacetate → 6-bromo-2,3-dimethyl-3H-imidazo[4,5-b]pyridine
Reaktionsgleichung
[Br:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH:8][CH3:9])=[N:6][CH:7]=1.CC(O[CH2:20][CH3:21])(OCC)OCC>CC(O)=O>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:20]([CH3:21])[N:8]([CH3:9])[C:5]2=[N:6][CH:7]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a suspension of 5-bromo-N2-methylpyridine-2,3-diamine (510 mg, 2.51 mmol) in AcOH (20 mL) was added MeC(OEt)3 (1 mL) and the solution was warmed to 80° C. for 2 hours. The reaction mixture was allowed to cool to room temperature and was concentrated in vacuo. The crude residue was purified by silica gel column chromatography (0-25% THF/CH2Cl2 gradient) to afford the desired product. 1H NMR (400 MHz, CDCl3) δ 8.36 (d, J=1.8 Hz, 1H), 8.06 (d, J=1.9 Hz, 1H), 3.80 (s, 3H), 2.65 (s, 3H).