Acetonitrile → HCID 178468567, compound

HRID 1501592Notes

Reaction equation

HRID 1501592 reaction equation
O[C:2]1[CH:3]=[C:4]([C:12]([O-:14])=[O:13])[C:5]2[C:10]([CH3:11])=[N:9][NH:8][C:6]=2[N:7]=1.P(Br)(Br)([Br:17])=O.[C:20](#N)[CH3:21]>>[Br:17][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH2:20][CH3:21])=[O:13])[C:5]2[C:10]([CH3:11])=[N:9][NH:8][C:6]=2[N:7]=1

Participants

4

Reactant 3

HCID 6342Acetonitrile2×HCID 24613Phosphorus oxybromideHCID 178434478HCID 178434478, compound

Product 1

HCID 178468567HCID 178468567, compoundYield 77.8%

Procedure

6-Hydroxy-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (2.5 g, 11.3 mmol) was suspended in acetonitrile (25 mL) and POBr3 (6.5 g, 22.6 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 and 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 target compound (2.5 g, 77.8%).

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-9c353c0956294c569038b9dbc2629608
Source dataset
uspto-grants-2015_12
Patent number
US09206157B2

Reaction notes

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