5-Nitrofurfural → HCID 86623875, compound

HRID 1696637Notes

Reaction equation

HRID 1696637 reaction equation
[N:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[NH:3][C:2]=1[SH:10].[H-].[Na+].[N+]([C:16]1[O:20][C:19]([CH:21]=[O:22])=[CH:18][CH:17]=1)([O-])=O>O1CCCC1>[N:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[NH:3][C:2]=1[S:10][C:16]1[O:20][C:19]([CH:21]=[O:22])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 127745-NitrofurfuralHCID 24758Sodium hydrideHCID 178527808HCID 178527808, compound

Product 1

HCID 86623875HCID 86623875, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 16 h, upon which it
  2. additionis poured on ice
  3. extractionextracted 3 times with ethyl acetate
  4. filtrationfiltered
  5. washThe filtrate is washed with brine
  6. customdried on magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe 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)
  10. additionThe fractions containing the desired product
  11. concentrationconcentrated to dryness under reduced pressure
  12. customThe residue is triturated in diethyl ether
  13. filtrationfiltered
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-75aeb1af796344d0949c6197134422a1
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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