Bromine → ethyl 3,6-dibromo-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 1909188Notes

Reaction equation

HRID 1909188 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.[Br:19]Br>C(O)(=O)C>[Br:19][C:10]1[C:5]2[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:3][C:2]([Br:1])=[N:7][C:6]=2[N:8]([CH:11]([CH3:13])[CH3:12])[N:9]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 86703408ethyl 6-bromo-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 86703410ethyl 3,6-dibromo-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylateYield 48%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of ethyl 6-bromo-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (2 g, 6.43 mmol) in acetic acid (6 mL) was added bromine (5.14 g, 32.15 mmol) at 0° C. Resulting reaction mass was stirred at room temperature for 3 h. Reaction was monitored by TLC. On completion, reaction was quenched with ice, NaHCO3 solution was added to it. Extraction was carried out using ethyl acetate; the combined organic layers were washed with water, brine and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure and residue was purified by silica gel column chromatography to obtain the desired intermediate (1.2 g, 48%).

Workup

  1. customResulting
  2. customreaction mass
  3. customReaction
  4. customOn completion, reaction
  5. customwas quenched with ice, NaHCO3 solution
  6. additionwas added to it
  7. extractionExtraction
  8. washthe combined organic layers were washed with water, brine
  9. dry with materialdried over anhydrous Na2SO4
  10. customSolvent was removed under reduced pressure and residue
  11. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c71acde87a304decac48180232677bca
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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