Methanol → (3-Iodo-1H-pyrazolo[3,4-b]pyridin-1-yl)acetic acid

HRID 503879Notes

Reaction equation

HRID 503879 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][C:12]([O:14]CC)=[O:13])[N:3]=1.CO.[Li+].[OH-]>C1COCC1>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][C:12]([OH:14])=[O:13])[N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 57642768Ethyl (3-iodo-1H-pyrazolo[3,4-b]pyridin-1-yl)acetate

Product 1

HCID 57642775(3-Iodo-1H-pyrazolo[3,4-b]pyridin-1-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (3-Iodo-pyrazolo[3,4-b]pyridin-1-yl)-acetate (11 g, 33 Mmol, 1 equiv) was dissolved in 50 mL of THF and 50 mL of MeOH to the solution was added 40 mL of 1N LiOH for 3 h. The organic solvents were evaporated and the remaining aqueous phase was neutralized with 1N HCl to a pH of about 1 which resulted in the precipitation of the desired product as a white solid was filtered and air dried to give (3-iodo-pyrazolo[3,4-b]pyridin-1-yl)-acetic acid.

Workup

  1. customThe organic solvents were evaporated

Sources & evidence

ORD record
ord-deb04ab868544c37a6f63272f14c05f6
Source dataset
uspto-grants-2010_08
Patent number
US07777035B2

Reaction notes

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