Sodium Hydroxide → 4-Chloro-2-methyl-2H-pyrazolo[3,4-b]pyridine

HRID 607154Notes

Reaction equation

HRID 607154 reaction equation
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([NH:5][CH:6]=[CH:7][C:8]2=O)=[N:3]1.P(Cl)(Cl)([Cl:14])=O.[OH-].[Na+]>>[Cl:14][C:8]1[C:9]2[C:4](=[N:3][N:2]([CH3:1])[CH:10]=2)[N:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 1364007322-Methyl-2,7-dihydro-pyrazolo[3,4-b]pyridin-4-one

Product 1

HCID 668084904-Chloro-2-methyl-2H-pyrazolo[3,4-b]pyridineYield 88%

Procedure

A mixture of the product of Example 8b (0.177 g, 1.19 mmol) and phosphorus oxychloride (3 mL) was heated under reflux for 30 min and then cooled to room temperature. The reaction mixture was poured over ice, taken to pH 8 by the addition of 1N aqueous sodium hydroxide solution, and extracted with dichloromethane (3×30 mL). The combined organic phase was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure to provide the title compound (0.170 g, 88% yield).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 min
  3. additionThe reaction mixture was poured over ice
  4. extractionextracted with dichloromethane (3×30 mL)
  5. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d59231ea5c2146ea98c4425d194d27d5
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

Loading…