Hydrochloric Acid → HCID 178524942, compound

HRID 1916455Notes

Reaction equation

HRID 1916455 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]([O:13]C)=[O:12])=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.Cl>[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]([OH:13])=[O:12])=[N:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178499173HCID 178499173, compound

Product 1

HCID 178524942HCID 178524942, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (XVII) (70 mg, 0.27 mmol) in aqueous 1N NaOH solution (20 mL) was heated at 90° C. for 3 h until the solution became clear. The solution was then cooled to 0° C. and acidified with a 10% HCl solution. The solids formed were filtered, washed with cold water and dried at room temperature under vacuum to give 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (XVIII) as a white solid (60 mg, 0.25 mmol, 92% yield). 1H NMR (CDCl3) δ ppm 8.58 (d, J=3.01 Hz, 1H), 8.66 (d, J=3.01 Hz, 1H); ESIMS found for C7H4BrN3O2 m/z 242.1 (M+H).

Workup

  1. temperatureThe solution was then cooled to 0° C.
  2. customThe solids formed
  3. filtrationwere filtered
  4. washwashed with cold water
  5. customdried at room temperature under vacuum

Sources & evidence

ORD record
ord-b1a477287e564cec9250cbb623709c81
Source dataset
uspto-grants-2013_12
Patent number
US08618128B1

Reaction notes

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