HCID 59389399, compound → 3-Chloro-2-ethyl-4-hydroxy-pyrazolo[1,5-a]pyridine

HRID 2357896Notes

Reaction equation

HRID 2357896 reaction equation
[Cl:1][C:2]1[C:3]([CH2:13][CH3:14])=[N:4][N:5]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11]C)[C:6]=12.[Br-].[Br-].[Br-].B>ClCCl>[Cl:1][C:2]1[C:3]([CH2:13][CH3:14])=[N:4][N:5]2[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:6]=12

Participants

4

Conditions

Temperature
0 °C

Procedure

The compound of Example 65 (3.07 g) was dissolved in dichloromethane (40 mL) in an argon atmosphere. While this solution was kept at 0° C., borane tribromide (17.6 mL, 1.0 mol/mL dichloromethane solution) was added and the mixture was stirred for 26 hours at 0° C. to reflux temperature. Subsequently, the reaction was terminated by adding water and the mixture was extracted three times with ethylacetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure to afford the title compound as a yellow powder (2.91 g).

Workup

  1. customwas kept at 0° C.
  2. temperatureto reflux temperature
  3. customSubsequently, the reaction was terminated
  4. additionby adding water
  5. extractionthe mixture was extracted three times with ethylacetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-90a9d65f845943babf6210b568f9ad1f
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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