3-Ethylsulfanyl-imidazo[1,5-a]pyridine-5-carbaldehyde → Imidazo[1,5-a]pyridine-5-carbaldehyde

HRID 280202Notes

Reaction equation

HRID 280202 reaction equation
[CH:1]([C:3]1[N:8]2[C:9](SCC)=[N:10][CH:11]=[C:7]2[CH:6]=[CH:5][CH:4]=1)=[O:2]>C(O)(C)C.[Ni]>[CH:1]([C:3]1[N:8]2[CH:9]=[N:10][CH:11]=[C:7]2[CH:6]=[CH:5][CH:4]=1)=[O:2]

Participants

4

Reactant 1

HCID 132061623-Ethylsulfanyl-imidazo[1,5-a]pyridine-5-carbaldehyde

Product 1

HCID 13206163Imidazo[1,5-a]pyridine-5-carbaldehyde

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 3776IsopropanolSolvent

Procedure

To a solution of 20 g of 5-formyl-3-ethylthioimidazo[1,5-a]pyridine in 200 ml of isopropanol is added approximately 15 g of Raney nickel. The reaction mixture is stirred and heated at reflux temperature for 16 hours. The catalyst is removed by filtration through celite. The filtrate is evaporated under reduced pressure to yield an oily residue. This is purified by column chromatography on silica gel using a mixture of diethyl ether and ethyl acetate (2:1) as eluent. Evaporation of the solvent under reduced pressure yields 5-formylimidazo[1,5-a]pyridine melting at 138°-140°.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 16 hours
  3. customThe catalyst is removed by filtration through celite
  4. customThe filtrate is evaporated under reduced pressure
  5. customto yield an oily residue
  6. customThis is purified by column chromatography on silica gel using
  7. additiona mixture of diethyl ether and ethyl acetate (2:1) as eluent
  8. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-8172b72dadb84d23a6256413e4863b03
Source dataset
uspto-grants-1986_05
Patent number
US04588732

Reaction notes

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