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

HRID 1501556Notes

Reaction equation

HRID 1501556 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-5d6b979615794ff991666f07c2d92494
Source dataset
uspto-grants-2015_12
Patent number
US09206157B2

Reaction notes

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