反应详情

1H-Imidazo[4,5-b]pyridine-2-thiol (1.51 g, 10.0 mmol) is suspended into 80 mL of tetrahydrofuran under argon. Then, 0.72 g (15.0 mmol) of sodium hydride is added. The reaction mixture is stirred at room temperature until gas evolution has ceased. 5-Nitro-2-furaldehyde (1.41 g, 10.0 mmol) is then added and the reaction mixture is stirred at room temperature for 2.5 h, upon which it is poured on ice and extracted 3 times with ethyl acetate. The organic extracts are combined, washed with brine, dried on magnesium sulfate, filtered and concentrated under reduced pressure. The residue is recrystallized from ethyl acetate, filtered, washed with ethyl acetate and dried under reduced pressure. 1.34 g of 5-(1H-imidazo[4,5-b]pyridin-2-ylsulfanyl)-furan-2-carbaldehyde is obtained as a crystalline light-brown powder. mp: 188° C.

1. stirringthe reaction mixture is stirred at room temperature for 2.5 h, upon which it
2. additionis poured on ice
3. extractionextracted 3 times with ethyl acetate
4. washwashed with brine
5. customdried on magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue is recrystallized from ethyl acetate
9. filtrationfiltered
10. washwashed with ethyl acetate
11. customdried under reduced pressure