Sodium Hydroxide → 6-Chloro-1H-pyrrolo[2,3-b]pyridine

HRID 1749801Notes

Reaction equation

HRID 1749801 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8](C(OC)=O)[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15013891methyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 113441186-Chloro-1H-pyrrolo[2,3-b]pyridineYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The synthesis was performed with reference to the known literature (International Patent Publication WO2008/080015). A solution of methyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (0.37 g, 1.8 mmol) in methanol (10 mL) was added with 5 N aqueous sodium hydroxide (2.0 mL), and the mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, the residue was added with water, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 6-chloro-1H-pyrrolo[2,3-b]pyridine (0.26 g, 95%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was added with water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe resulting organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-609d19aea12f45a585b0f3328f99ba74
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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