Hydrochloric Acid → 5-chloro-1H-pyrrolo(3,2-b)pyridine-2-carboxylic acid

HRID 628350Notes

Reaction equation

HRID 628350 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C:20]([O:22]CC)=[O:21])[N:10](S(C3C=CC=CC=3)(=O)=O)[C:5]2=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C:20]([OH:22])=[O:21])[NH:10][C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53816579Ethyl 1-(benzenesulfonyl)-5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylate

Product 1

HCID 116655855-chloro-1H-pyrrolo(3,2-b)pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of ethyl 5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylate (2.50 g, 6.85 mmol, prepared as in Example 82, Step 1) in THF (20 mL) was added 1.0 M NaOH (20 mL, 20 mmol) and the reaction was stirred overnight. Concentrated HCl was added to acidify (to pH ˜2). The product was extracted with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered and concentrated to afford a white solid. The yield was close to theoretical and the product was used without further purification.

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. dry with materialThe combined extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford a white solid
  6. customThe yield was close to theoretical and the product
  7. customwas used without further purification

Sources & evidence

ORD record
ord-335333998bf7495bbc0b284d02234e53
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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