Phosphorus oxychloride → 4-Chloro-1H-pyrrolo[2,3-b]pyridine

HRID 1020904Notes

Reaction equation

HRID 1020904 reaction equation
[NH:1]1[C:5]2=[N+:6]([O-])[CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[C:4]=1[CH:3]=[CH:2][NH:1]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526243HCID 178526243, compound

Product 1

HCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Procedure

A mixture of 1H-pyrrolo[2,3-b]pyridin-7-oxide (step 1)(10.0 g, 74.5 mmol) in phosphorous oxychloride (50 mL) was heated to reflux. After 12 h the excess phosphorous oxychloride was evaporated under reduced pressure and the residue was stirred in saturated aqueous sodium bicarbonate (250 mL) for one hour. The solid was collected by suction filtration, washed with water to neutrality, and air-dried to afford 9.8 g of 4-choro-7-azaindole as an off-white solid; MS (m/z) 153/155 (M+H).

Workup

  1. temperaturewas heated to reflux
  2. customAfter 12 h the excess phosphorous oxychloride was evaporated under reduced pressure
  3. filtrationThe solid was collected by suction filtration
  4. washwashed with water to neutrality
  5. customair-dried

Sources & evidence

ORD record
ord-ccd0240336d04444b787caf0b50dca6a
Source dataset
uspto-grants-2014_05
Patent number
US08716493B2

Reaction notes

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