Potassium Hydroxide → CID 87191335

HRID 2089002

Reaction equation

HRID 2089002 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10](S(C3C=CC=CC=3)(=O)=O)[CH:9]=2)[CH:5]=[C:4]([Cl:26])[N:3]=1.[OH-].[K+]>C(O)C.O>[Cl:26][C:4]1[CH:5]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)[CH:7]=[C:2]([Cl:1])[N:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 866498693-(2,6-dichloropyridin-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 87191335CID 87191335Yield 88.3%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of Example 7a (5.72 g, 15 mmol) in 60 mL ethanol/water (5/1) was added powdered KOH (2 g, 35 mmol). The resulting solution was heated at 40° C. for 2 hours. Most of the solvent was removed in vacuo, and the residue was diluted with ethyl acetate. A solid was filtered from the material and discarded. The organics were washed with water, brine, dried over MgSO4, filtered, and concentrated. The crude material was triturated with dichloromethane and filtered, giving 3.5 g of the title compound as a white solid. MS (ESI+) m/z 263.6 (M+H)+.

Workup

  1. customMost of the solvent was removed in vacuo
  2. additionthe residue was diluted with ethyl acetate
  3. filtrationA solid was filtered from the material
  4. washThe organics were washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was triturated with dichloromethane
  9. filtrationfiltered

Sources & evidence

ORD record
ord-dbe488fa85d8415a9d7ac19307942f55
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Linked notes

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