Sulfuryl chloride → 2-Chloro-1H-pyrrolo[2,3-b]pyridine-3-acetonitrile

HRID 1756101Notes

Reaction equation

HRID 1756101 reaction equation
[C:1]([CH2:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)#[N:2].S(Cl)([Cl:16])(=O)=O>C(O)(=O)C>[Cl:16][C:5]1[NH:6][C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:12]2[C:4]=1[CH2:3][C:1]#[N:2]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 21911990(1H-Pyrrolo[2,3-b]pyridin-3-yl)acetonitrile

Product 1

HCID 193925832-Chloro-1H-pyrrolo[2,3-b]pyridine-3-acetonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-cyanomethylpyrrolo[2,3-b]pyridine (1,55 g, 0.098 mol) was treated in 5 ml acetic acid with an equimolecular amount of sulfurylchloride at 0° C. for 5 min. The mixture was allowed to warm to room temperature and was stirred 5 min. After evaporation the residue was dissolved in methylen chloride and was treated with bicarbonate. The organic layer was separated, dried over Na2SO4 and the solvent was removed under reduced pressure. Chromatography on silica gel eluting with ethyl acetate gave the desired product. (0,4 g 21%).

Workup

  1. customAfter evaporation the residue
  2. dissolutionwas dissolved in methylen chloride
  3. additionwas treated with bicarbonate
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-35ec616ca9f1410dbe3bae3a04a93e87
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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