Sodium Hydroxide → HCID 67198692, compound

HRID 910254Notes

Reaction equation

HRID 910254 reaction equation
FC1C=CC=CC=1[N:8]1[C:12]2[N:13]([CH3:18])[C:14](=[O:17])[CH:15]=[CH:16][C:11]=2[CH:10]=[N:9]1.[C:19]([N:23]1[C:27]2[N:28]([CH3:33])[C:29](=[O:32])[CH:30]=[CH:31][C:26]=2[CH:25]=[N:24]1)([CH3:22])([CH3:21])[CH3:20].[Br:34]Br.[OH-:36].[Na+]>CC(O)=O.O>[C:19]([N:23]1[C:27]2[N:28]([CH3:33])[C:29](=[O:32])[CH:30]=[CH:31][C:26]=2[CH:25]=[N:24]1)([CH3:22])([CH3:21])[CH3:20].[C:14]([OH:17])(=[O:36])[CH3:15].[Br:34][C:15]1[C:14](=[O:17])[N:13]([CH3:18])[C:12]2[NH:8][N:9]=[CH:10][C:11]=2[CH:16]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 67198695HCID 67198695, compoundHCID 67200050HCID 67200050, compound

Product 2

HCID 67198692HCID 67198692, compoundHCID 67200050HCID 67200050, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1-Tert-butyl-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one was prepared in a fashion similar to that described for 1-(2-fluorophenyl)-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (155 mg) as a light yellow crystalline solid (Example 1-step 3). 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. extractionIt was extracted with 2×50 mL EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo (rotovap)

Sources & evidence

ORD record
ord-1bec27c88d094589951fba208a79d335
Source dataset
uspto-grants-2011_09
Patent number
US08022085B2

Reaction notes

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