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

HRID 16420Notes

Reaction equation

HRID 16420 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 (from example XXXVII) is suspended in 5 ml of phosphoryl chloride. 2 ml of chloroform are then added, and the mixture is heated under reflux 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 over 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. temperatureunder reflux overnight
  3. customThe phases are separated
  4. washthe aqueous phase is washed with ethyl acetate
  5. dry with materialThe organic phases are dried over 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-165fed6cac864e65a35de3803583c8e3
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Reaction notes

Loading…