Sodium Hydroxide → HCID 86689858, compound

HRID 2409042Notes

Reaction equation

HRID 2409042 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[N:12](S(C3C=CC(C)=CC=3)(=O)=O)[CH:11]=[CH:10][C:5]2=[N:6][C:7]=1[C:8]#[N:9].[OH-].[Na+]>CO.O>[F:1][C:2]1[CH:3]=[C:4]2[NH:12][CH:11]=[CH:10][C:5]2=[N:6][C:7]=1[C:8]#[N:9]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86689854HCID 86689854, compound

Product 1

HCID 86689858HCID 86689858, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile (2742 mg, 7.85 mmol) in MeOH (20 mL) and water (20 mL) was added NaOH (628 mg 15.7 mmol). The mixture was stirred at RT for 1 h. The reaction mixture was quenched by adding a sat'd aq. NH4Cl and extracted with EtOAc. The extract was dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by SiO2 chromatography eluting with a petroleum ether:EtOAc gradient (10:1-0:1) to afford 758 mg (60%) of 6-fluoro-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile. MS (ESI): m/z=162.3 [M+1]+.

Workup

  1. customThe reaction mixture was quenched
  2. additionby adding a sat'd aq. NH4Cl
  3. extractionextracted with EtOAc
  4. dry with materialThe extract was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by SiO2 chromatography
  8. washeluting with a petroleum ether

Sources & evidence

ORD record
ord-12efd4e772e54580829ba49cd4d10e94
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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