Ethyl Acetate → 6-Chloro-1H-pyrrolo[2,3-b]pyridine
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- additionwas added to the aqueous layer
- extractionThe aqueous layer was extracted with ethyl acetate
- washthe combined organic layers were washed with sat. NaHCO3
- dry with materialdried over Na2SO4
- filtrationThe mixture was filtered
- 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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