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

HRID 16404

Reaction equation

HRID 16404 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.N.P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:1][CH:2]=[CH:3][C:4]=12

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 178526243HCID 178526243, compound

Product 1

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

Procedure

100 mg (0.76 mmol) of 1H-pyrrolo[2,3-b]pyridine 7-oxide (from example XV) in 3 ml of phosphorus oxychloride are heated at reflux until a clear solution is formed. After cooling to room temperature, the reaction mixture is carefully hydrolyzed with ice. The mixture is made alkaline using ammonia and extracted repeatedly with ethyl acetate. The organic phase is washed with water and saturated sodium chloride solution. After drying over magnesium sulfate, the solvent is removed under reduced pressure. This gives a yellow oil which is purified by preparative HPLC.

Workup

  1. temperatureat reflux until a clear solution
  2. customis formed
  3. extractionextracted repeatedly with ethyl acetate
  4. washThe organic phase is washed with water and saturated sodium chloride solution
  5. dry with materialAfter drying over magnesium sulfate
  6. customthe solvent is removed under reduced pressure
  7. customThis gives a yellow oil which
  8. customis purified by preparative HPLC

Sources & evidence

ORD record
ord-f0cc1ae22c5547509708043e55f43d34
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Linked notes

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