Sulfuryl chloride → 2-chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 1756098Notes

Reaction equation

HRID 1756098 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.S(Cl)([Cl:14])(=O)=O>C(O)(=O)C>[Cl:14][C:3]1[NH:4][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:10]2[C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 109314713-Methyl-7-azaindole

Product 1

HCID 193925862-chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-methylpyrrolo[2,3-b]pyridine (0,5 g 0.0038 mol) was treated in 2 ml acetic acid with an equimolecular amount of sulfuryl chloride at 0° C. for 5 min. The mixture was allowed to warm to room temperature and was stirred for 5 min. After evaporation the residue was dissolved in methylene chloride and was treated with bicarbonate. The organic layer was separated, dried and removed under reduced pressure. Chromatography on silica gel eluting with ethyl acetate gave the desired product. (0,18 g 29%).

Workup

  1. customAfter evaporation the residue
  2. dissolutionwas dissolved in methylene chloride
  3. additionwas treated with bicarbonate
  4. customThe organic layer was separated
  5. customdried
  6. customremoved under reduced pressure

Sources & evidence

ORD record
ord-51ced4447db94485886c5ff981b71509
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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