Chloroform → 4-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 2192160Notes

Reaction equation

HRID 2192160 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[N+:6]([O-])[CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.C(Cl)(Cl)[Cl:13].C(=O)([O-])[O-].[Na+].[Na+]>P(Cl)(Cl)(Cl)=O>[Cl:13][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:4][CH:3]=[C:2]([CH3:1])[C:10]=12

Participants

5

Reactant 3

HCID 6212ChloroformHCID 10340Sodium CarbonateHCID 178430808HCID 178430808, compound

Product 1

HCID 179793234-Chloro-3-methyl-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

1.00 g (6.75 mmol) of 3-methyl-1H-pyrrolo[2,3-b]pyridine 7-oxide is suspended in 5 ml of phosphoryl chloride. 2 ml of chloroform are then added, and the mixture is heated at reflux temperature overnight. The mixture is allowed to cool to RT and poured into ethyl acetate/ice-water. Solid sodium carbonate is then added. The phases are separated and the aqueous phase is washed with ethyl acetate. The organic phases are dried with sodium sulfate and concentrated. The residue is purified by column chromatography (silica gel 60, mobile phase: cyclohexane/methanol=4:1).

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux temperature overnight
  3. customThe phases are separated
  4. washthe aqueous phase is washed with ethyl acetate
  5. dry with materialThe organic phases are dried with sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is purified by column chromatography (silica gel 60, mobile phase: cyclohexane/methanol=4:1)

Sources & evidence

ORD record
ord-cbfc7a43a91b497eb65cd0c31c0e7630
Source dataset
uspto-grants-2012_12
Patent number
US08329716B2

Reaction notes

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