Hydrochloric Acid → 3-[3-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridin-1-yl]phenoxyacetic acid

HRID 1084847Notes

Reaction equation

HRID 1084847 reaction equation
[OH-].[Na+].C(O)C.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22]3[CH:23]=[C:24]([CH:32]=[CH:33][CH:34]=3)[O:25][CH2:26][C:27]([O:29]CC)=[O:28])[N:14]=2)=[CH:9][CH:8]=1.Cl>O.O1CCOCC1>[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22]3[CH:23]=[C:24]([CH:32]=[CH:33][CH:34]=3)[O:25][CH2:26][C:27]([OH:29])=[O:28])[N:14]=2)=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 14796397ethyl 3-[3-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridin-1-yl]phenoxyacetate

Product 1

HCID 147963983-[3-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridin-1-yl]phenoxyacetic acidYield 64.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

In 5 ml of water was dissolved 0.97 g of sodium hydroxide, whereto 100 ml of ethanol was added. Thereto was added a solution of 8.0 g of ethyl 3-[3-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridin-1-yl]phenoxyacetate dissolved in 60 ml of dioxane while stirring. After the mixture was stirred at room temperature for 4 hours, about 500 ml of water was added thereto and the mixture was neutralized with dilute hydrochloric acid. The resulting crystals were collected by filtration and recrystallized from dioxane to give 4.8 g of 3-[3-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridin-1-yl]phenoxyacetic acid, m.p. 225°-226° C.

Workup

  1. additionwas added
  2. stirringAfter the mixture was stirred at room temperature for 4 hours
  3. filtrationThe resulting crystals were collected by filtration
  4. customrecrystallized from dioxane

Sources & evidence

ORD record
ord-075ca88072b54f258602ec2a0720b8f2
Source dataset
uspto-grants-1991_04
Patent number
US05006520

Reaction notes

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