Water → HCID 12617474, compound

HRID 2051123Notes

Reaction equation

HRID 2051123 reaction equation
[CH:1]1[N:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[CH3:10][S:11]SC.O>O1CCCC1.C([Li])CCC>[CH3:10][S:11][C:3]1[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=[CH:1][N:2]=1

Participants

6

Reactant 3

HCID 962WaterHCID 12232Dimethyl DisulfideHCID 274090Imidazo(1,5-a)pyridine

Product 1

HCID 12617474HCID 12617474, compoundYield 104.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 178418339ButyllithiumSolvent

Procedure

To a solution of 1.63 g of imidazo[1,5-a]pyridine in 20 ml of tetrahydrofuran, 11 ml of n-butyl lithium (1.6N-hexane solution) is added below 70° C. during 15 minutes under nitrogen gas atmosphere. After stirring the mixture for an hour at the same temperature, a solution of 1.7 g of dimethyldisulfide in 10 ml of tetrahydrofuran is dropwise added during 30 minutes and continued to stir for 30 minutes. The mixture added with water is extracted with ether. The extract is dried over anhydrous magnesium sulfate and distilled to remove ether. The residue is purified by silica gel chromatography (eluent: chlooform-ethylacetate) to give 2.37 g of the oily title compound.

Workup

  1. stirringto stir for 30 minutes
  2. extractionis extracted with ether
  3. dry with materialThe extract is dried over anhydrous magnesium sulfate
  4. distillationdistilled
  5. customto remove ether
  6. customThe residue is purified by silica gel chromatography (eluent: chlooform-ethylacetate)

Sources & evidence

ORD record
ord-847ff9d015964196ad7c858c8a615f65
Source dataset
uspto-grants-1991_05
Patent number
US05017212

Reaction notes

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