Water → HCID 68701294, compound

HRID 1988862Notes

Reaction equation

HRID 1988862 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:26]#N)[C:15]=2[O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:10]([CH3:28])=[C:9]1[CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:30].[K+].[OH2:32]>C(O)C>[CH2:1]([N:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:26]([OH:32])=[O:30])[C:15]=2[O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:10]([CH3:28])=[C:9]1[CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 14797Potassium HydroxideHCID 68705257HCID 68705257, compound

Product 1

HCID 68701294HCID 68701294, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Benzyl-7-(4-fluorobenzyloxy)-2,3-dimethyl-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile (500 mg, 1.30 mmol) prepared in Example 276 was diluted with a mixture of ethanol (8 ml) and water (2 ml). Potassium hydroxide (650 mg, 13.0 mmol) was added to the solution, which was then refluxed for 24 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The separated organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/methanol=5/1, (v/v)) to give 280 mg of the titled compound as a white solid.

Workup

  1. temperaturewas then refluxed for 24 hours
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe separated organic layer was dried on anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/methanol=5/1, (v/v))

Sources & evidence

ORD record
ord-1e6bb6737b024a109e6eb05630ac5abc
Source dataset
uspto-grants-2010_01
Patent number
US07642269B2

Reaction notes

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