5-Nitrofurfural → HCID 86623875, compound

Participants

Reaction Steps

3H-Imidazo[4,5-c]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 16 h, upon which it is poured on ice and extracted 3 times with ethyl acetate. The organic extracts are combined and filtered. The filtrate is washed with brine, dried on magnesium sulfate, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a prepacked 70 g 15-40 μm silica gel cartridge (eluting solvent: dichloromethane/acetonitrile/methanol from 75/20/5 to 90/0/10 v/v/v; rate: 40 mL/min). The fractions containing the desired product are combined and concentrated to dryness under reduced pressure. The residue is triturated in diethyl ether, filtered and dried under reduced pressure. 270 mg of 5-(3H-imidazo[4,5-c]pyridin-2-ylsulfanyl)-furan-2-carbaldehyde are obtained as a crystalline yellow powder. LCMS: m/z 246: [M+H]+ (base peak); m/z 244: [M−H]− (base peak).

Provenance & Evidence