Water → HCID 67198692, compound

HRID 2261256Notes

Reaction equation

HRID 2261256 reaction equation
C([N:5]1[C:9]2[N:10]([CH3:15])[C:11](=[O:14])[CH:12]=[CH:13][C:8]=2[CH:7]=[N:6]1)(C)(C)C.[Br:16]Br.[OH2:18].[OH-].[Na+]>CC(O)=O>[C:11]([OH:14])(=[O:18])[CH3:12].[Br:16][C:12]1[C:11](=[O:14])[N:10]([CH3:15])[C:9]2[NH:5][N:6]=[CH:7][C:8]=2[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24408BromineHCID 67200050HCID 67200050, compound

Product 1

HCID 67198692HCID 67198692, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1-tert-butyl-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (240 mg, 1.17 mmol) in glacial AcOH (5.5 mL) at RT was added bromine (0.060 mL, 1169 μmol) slowly. An orange suspension resulted and it was allowed to stir at RT for 1 h. 5.0 mL water was added, and the pH was adjusted to pH 6 using 5 N NaOH, It was extracted with 2×50 mL EtOAc, dried over MgSO4, filtered and concentrated in vacuo (rotovap) affording 5-bromo-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one acetic acid adduct (305 mg) as a beige solid. MS (ESI, pos.ion) m/z: 227.9 (M+1) and 229.9 (M+1). This crude product was used in the next step.

Workup

  1. customAn orange suspension resulted
  2. extractionwas extracted with 2×50 mL EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo (rotovap)

Sources & evidence

ORD record
ord-30bca9abfefb44ba82b5fb1ddc29d4fd
Source dataset
uspto-grants-2010_12
Patent number
US07846944B2

Reaction notes

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