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

HRID 1765617Notes

Reaction equation

HRID 1765617 reaction equation
[NH+:1]1([O-])[C:5]2=[N:6][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[NH:1][CH:2]=[CH:3][C:4]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 219590977-aza-1H-indole N-oxide

Product 1

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

Procedure

1H-Pyrrolo[2,3-b]pyridine-N-oxide (Reference Example 65) (10.0 g) in phosphorous oxychloride (75 mL) was heated at reflux for 8 hours. The excess phosphorous oxychloride was evaporated and the residue was taken up in water and the solution was brought to a pH=8–9, the resultant precipitate was filtered and air-dried to give the title compound as an off-white solid (10.2 g). MS: 152 (MH+). 1H NMR (CDCl3): δ 8.2 (d, 1H), 7.5 (d, 1H), 7.2 (d, 2H), 6.6 (d, 2H).

Workup

  1. temperatureat reflux for 8 hours
  2. customThe excess phosphorous oxychloride was evaporated
  3. filtrationthe resultant precipitate was filtered
  4. customair-dried

Sources & evidence

ORD record
ord-0e801e36afcb4b9e9010c7ba3b4ba7c8
Source dataset
uspto-grants-2007_06
Patent number
US07227020B2

Reaction notes

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