Dimethyl Disulfide → 2-(2-Methylthiophenyl)imidazo[1,2-a]pyridine

HRID 1199473Notes

Reaction equation

HRID 1199473 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]2[CH:16]=1.C([Li])CCC.[CH3:22][S:23]SC>CCOCC>[CH3:22][S:23][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]2[CH:16]=1

Participants

5

Reactant 3

HCID 12232Dimethyl DisulfideHCID 28623882-(2-Bromophenyl)imidazo[1,2-a]pyridineHCID 178418339Butyllithium

Product 1

HCID 198667372-(2-Methylthiophenyl)imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The product of step (a) above (546 mg) was dissolved in dry ether (10 ml) and stirred under a nitrogen atmosphere at -60°. A solution of n-butyl lithium (1.25 ml of 1.6 M) was added dropwise. After stirring for 5 minutes methyl disulphide (179 ml) was added dropwise and the mixture stirred for a further 45 minutes. The mixture was allowed to warm up to room temperature then quenched with water. The layers were separated and the aqueous layer extracted with ethyl acetate. The combined organic solution was washed with water and brine then dried and evaporated to leave the sub-title compound as a gum. MS MW 240 bp 207.

Workup

  1. additionwas added dropwise
  2. stirringthe mixture stirred for a further 45 minutes
  3. customthen quenched with water
  4. customThe layers were separated
  5. extractionthe aqueous layer extracted with ethyl acetate
  6. washThe combined organic solution was washed with water and brine
  7. customthen dried
  8. customevaporated

Sources & evidence

ORD record
ord-958596548dad4a7e90f0bd17ca0db982
Source dataset
uspto-grants-1990_02
Patent number
US04900751

Reaction notes

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