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

HRID 1756096Notes

Reaction equation

HRID 1756096 reaction equation
[CH3:1][C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1.S(Cl)([Cl:14])(=O)=O>C(O)(=O)C>[Cl:14][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:10][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 5830662-Methyl-7-azaindole

Product 1

HCID 193925933-Chloro-2-methyl-1H-pyrrolo[2,3-b]pyridineYield 51%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 0,7 g (5.3 mmol) of 2-methylpyrrolo[2,3-b]pyridine in 2,5 ml glacial acetic acid was added dropwise 0,8 g (5.9 mmol) of sulfuryl chloride at room temperature and with stirring. The reaction mixture was stirred for 1 hour. The solvent was evaporated and the residue was partitioned between methylene chloride and a saturated sodium bicarbonate solution. The organic layer was dried over sodium sulfate and the solvent was evaporated. The residue was crystallized from ether: ethyl acetate, 5:1 to give 0,45 g (51%) of the title compound.

Workup

  1. stirringThe reaction mixture was stirred for 1 hour
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between methylene chloride
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was crystallized from ether

Sources & evidence

ORD record
ord-42cda74b40074f0889feb7ddea03479e
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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