Ethyl Acetate → 6-Chloro-1H-pyrrolo[2,3-b]pyridine

HRID 748646Notes

Reaction equation

HRID 748646 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8](C(C3C=CC=CC=3)=O)[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.[OH-].[Na+].C(OCC)(=O)C>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

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 15013892(6-Chloro-1H-pyrrolo[2,3-b]pyridin-1-yl)(phenyl)methanone

Product 1

HCID 113441186-Chloro-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of (Intermediate C3) (3.12 mmol) in MeOH (90 mL) was treated with 1 M NaOH (30 mL) at rt for 18 h. The solution was freed of MeOH under reduced pressure and ethyl acetate was added to the aqueous layer. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with sat. NaHCO3, and dried over Na2SO4. The mixture was filtered and the solvent was evaporated to give a solid 6-chloro-1H-pyrrolo[2,3-b]pyridine (Intermediate C4).

Workup

  1. additionwas added to the aqueous layer
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic layers were washed with sat. NaHCO3
  4. dry with materialdried over Na2SO4
  5. filtrationThe mixture was filtered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-12104a8f793c40f4a9680a0d47d24369
Source dataset
uspto-grants-2008_07
Patent number
US07399868B2

Reaction notes

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