Lithium Hydroxide → (3-Chloro-2H-pyrazolo[3,4-b]pyridin-2-yl)acetic acid

HRID 930567Notes

Reaction equation

HRID 930567 reaction equation
C([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:14]([Cl:15])=[C:13]2[C:8]([N:9]=[CH:10][CH:11]=[CH:12]2)=[N:7]1)C.[OH-].[Li+]>CO>[Cl:15][C:14]1[N:6]([CH2:5][C:4]([OH:16])=[O:3])[N:7]=[C:8]2[C:13]=1[CH:12]=[CH:11][CH:10]=[N:9]2

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57642771Ethyl (3-chloro-2H-pyrazolo[3,4-b]pyridin-2-yl)acetate

Product 1

HCID 57642788(3-Chloro-2H-pyrazolo[3,4-b]pyridin-2-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3-Chloro-pyrazolo[3,4-b]pyridin-2-yl)-acetic acid ethyl ester was treated with 1N lithium hydroxide (LiOH) (1 equiv) in 1 mL of MeOH to provide 2-(3-Chloro-pyrazolo[3,4-b]pyridine-2-yl)-acetic acid, which was used as directly in subsequent reactions without further purification: LCMS (ES) M+H 212.0, Rf 0.34 min (Agilent Zorbax SB-C18, 2.1×50 mm, 5μ, 35° C., 1 ml/min flow rate, a 2.5 min gradient of 20% to 100% B with a 1.1 min wash at 100% B; A=0.1% formic acid/5% acetonitrile/94.9% water, B=0.1% formic acid/5% water/94.9% acetonitrile).

Sources & evidence

ORD record
ord-c589254e72de4602b56c3358413ff017
Source dataset
uspto-grants-2016_03
Patent number
US09296740B2

Reaction notes

Loading…