Water → 4-Chloro-1H-pyrrolo[2,3-B]pyridine-3-carbonitrile

HRID 1696195Notes

Reaction equation

HRID 1696195 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8](S(C3C=CC=CC=3)(=O)=O)[CH:9]=[C:10]([C:11]#[N:12])[C:3]=12.[OH-].[Na+].O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[C:10]([C:11]#[N:12])[C:3]=12

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 497590871H-Pyrrolo[2,3-B]pyridine-3-carbonitrile, 4-chloro-1-(phenylsulfonyl)-

Product 1

HCID 457903004-Chloro-1H-pyrrolo[2,3-B]pyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile was treated with 2M NaOH solution (4 ml) in tetrahydrofuran (8 ml) at ambient temperature for 1 hour. The reaction mixture was cooled and was added water. The aqueous layer was extracted with EtOAc. And the organic layer was washed with brine, dried over MgSO4 and concentrated. Resultings were purified by silica gel column chromatography to give 4-chloro-1H-pyrrolo[2,3-b]-pyridine-3-carbonitrile as colorless powder.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washAnd the organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customResultings were purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0cdd8dbf809e4beeb71196efdec39bcd
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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