Sodium Hydroxide → 1-benzyl-6-chloro-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 574992Notes

Reaction equation

HRID 574992 reaction equation
[OH-].[Na+].[CH2:3]([N:10]1[C:14]2[N:15]=[C:16]([Cl:24])[CH:17]=[C:18]([C:19]([O:21]CC)=[O:20])[C:13]=2[CH:12]=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])(O)=O.[Na+]>C1COCC1>[CH2:3]([N:10]1[C:14]2[N:15]=[C:16]([Cl:24])[CH:17]=[C:18]([C:19]([OH:21])=[O:20])[C:13]=2[CH:12]=[N:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 117778147ethyl 1-benzyl-6-chloro-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 1177780091-benzyl-6-chloro-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A molar solution of sodium hydroxide (116 mL/0.116 mol) is added to a solution of ethyl 1-benzyl-6-chloro-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (30.5 g/96.8 mmol) in 195 mL of THF. The mixture is stirred at ambient temperature for 2 hours and then run into a saturated aqueous solution of NaHCO3. The aqueous phase is washed with ethyl acetate and then acidified with a solution of KHSO4 (1 M) and extracted with EtOAc. The organic phase is dried over sodium sulphate and then concentrated to dryness. The product is taken up with diisopropyl ether, filtered, and then dried under vacuum to give 27.3 g of a pale yellow powder (yield: 98%).

Workup

  1. washThe aqueous phase is washed with ethyl acetate
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. concentrationconcentrated to dryness
  5. filtrationfiltered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-86af70aab5c24161956a91a4e773a549
Source dataset
uspto-grants-2015_05
Patent number
US09034898B2

Reaction notes

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