Sodium Hydroxide → phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone

HRID 1821841Notes

Reaction equation

HRID 1821841 reaction equation
[C:1]1([C:7]([C:9]2[N:17](S(C3C=CC=CC=3)(=O)=O)[C:12]3=[CH:13][N:14]=[CH:15][CH:16]=[C:11]3[CH:10]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CCO>[C:1]1([C:7]([C:9]2[NH:17][C:12]3=[CH:13][N:14]=[CH:15][CH:16]=[C:11]3[CH:10]=2)=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 689825291h-Pyrrolo[2,3-c]pyridine,2-benzoyl-1-(phenylsulfonyl)-

Product 1

HCID 57893467phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanoneYield 84.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Phenyl[1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridin-2-yl]methanone (Reference Example 13) (2.2 g, 6.1 mmol) and 10% aq NaOH (70 mL) in EtOH (135 mL) was heated to reflux. After 14 h, the mixture was concentrated under reduced pressure to remove most of the EtOH. The mixture was diluted with H2O (50 mL) and extracted with EtOAc (2×100 mL). The combined extracts were washed with saturated NaCl (25 mL), dried (Na2SO4) and concentrated under reduced pressure. Trituration in EtOAc/diethyl ether gave phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (1.14 g, 83%).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customto remove most of the EtOH
  3. additionThe mixture was diluted with H2O (50 mL)
  4. extractionextracted with EtOAc (2×100 mL)
  5. washThe combined extracts were washed with saturated NaCl (25 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eaaedbffbc1f4e0c9d736fc0419a3cf8
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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