Potassium Hydroxide → 4-Chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

HRID 490878Notes

Reaction equation

HRID 490878 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][N:5]=[C:4]2[N:13]([CH2:16][CH3:17])[N:14]=[CH:15][C:3]=12.[OH-].[K+]>O1CCOCC1.O>[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[C:4]2[N:13]([CH2:16][CH3:17])[N:14]=[CH:15][C:3]=12

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 10491120ethyl 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Product 1

HCID 183487784-Chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acidYield 77.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of Intermediate 1 (3.5 g) in dioxane (28 ml) was treated with potassium hydroxide (6.3 g) as a solution in water (20 ml). The mixture was stirred for 2 h, then concentrated in vacuo, acidified to pH 3 with 2M aqueous hydrochloric acid and extracted with ethyl acetate. The layers were separated, the organic layer dried over sodium sulphate, then concentrated in vacuo to afford Intermediate 11 as a white solid (2.4 g). LCMS showed MH+=226; TRET=2.62 min.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. customThe layers were separated
  4. dry with materialthe organic layer dried over sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-31aaac6ded3544c68e50a2a8c37ad576
Source dataset
uspto-grants-2009_05
Patent number
US07528148B2

Reaction notes

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