Phosphorus oxybromide → HCID 178468568, compound

HRID 1854079Notes

Reaction equation

HRID 1854079 reaction equation
[CH2:1]([C:3]1[C:11]2[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][C:8](O)=[N:7][C:6]=2[NH:5][N:4]=1)[CH3:2].P(Br)(Br)([Br:20])=O>C(#N)C>[Br:20][C:8]1[CH:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:11]2[C:3]([CH2:1][CH3:2])=[N:4][NH:5][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178469360HCID 178469360, compound

Product 1

HCID 178468568HCID 178468568, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Ethyl 3-ethyl-6-hydroxy-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (0.52 g, 2.21 mmol) was suspended in acetonitrile (6 mL) and POBr3 (1.27 g, 4.42 mmol) was added to it. The reaction mixture was refluxed for 6 h. On completion of reaction, acetonitrile was removed under reduced pressure and residue neutralized with saturated NaHCO3. Extraction was carried out using EtOAc; the combined organic layers were washed with water, brine and dried over anhydrous Na2SO4; filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to provide the desired intermediate (0.45 g, 68.5%).

Workup

  1. temperatureThe reaction mixture was refluxed for 6 h
  2. customwas removed under reduced pressure and residue
  3. extractionExtraction
  4. washthe combined organic layers were washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d3eb5810c7b94703b189c6dd06854f7a
Source dataset
uspto-grants-2015_02
Patent number
US08962620B2

Reaction notes

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