Sodium Hydroxide → 5-Chloro-1H-pyrrolo[3,2-b]pyridine-2-carbonitrile

HRID 628443Notes

Reaction equation

HRID 628443 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C:20]#[N:21])[N:10](S(C3C=CC=CC=3)(=O)=O)[C:5]2=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C:20]#[N:21])[NH:10][C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118159515HCID 118159515, compound

Product 1

HCID 918259655-Chloro-1H-pyrrolo[3,2-b]pyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Chloro-1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridine-2-carbonitrile (0.50 g, 1.6 mmol, from Step 1) in THF (10. mL) was treated with 1.0 M NaOH (10. mL, 10. mmol) until removal of phenylsulfonyl protecting group was complete as determined by LCMS. The reaction mixture was extracted with three portions of EtOAc. The combined organic extracts were dried over sodium sulfate, filtered and concentrated until solid product precipitated. The solid was collected via filtration and triturated with EtOAc. Yield: (0.21 g, 75%).

Workup

  1. extractionThe reaction mixture was extracted with three portions of EtOAc
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated until solid product
  5. customprecipitated
  6. filtrationThe solid was collected via filtration
  7. customtriturated with EtOAc

Sources & evidence

ORD record
ord-40eae511440941418ee7d59ca31acc13
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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