Phosphorus oxybromide → 4-bromo-1H-pyrazolo[4,3-c]pyridin-3-amine

HRID 1677635Notes

Reaction equation

HRID 1677635 reaction equation
P(Br)(Br)([Br:3])=O.[NH2:6][C:7]1[C:11]2[C:12](O)=[N:13][CH:14]=[CH:15][C:10]=2[NH:9][N:8]=1.C(=O)(O)[O-].[Na+]>>[Br:3][C:12]1[C:11]2[C:7]([NH2:6])=[N:8][NH:9][C:10]=2[CH:15]=[CH:14][N:13]=1

Participants

4

Reactant 3

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 178509212HCID 178509212, compound

Product 1

HCID 583807624-bromo-1H-pyrazolo[4,3-c]pyridin-3-amineYield 58.1%

Conditions

Temperature
70 °C

Procedure

To 3.5 g of POBr3 melted at 45° C. is added 0.4 g of 3-amino-1H-pyrazolo[4,3-c]pyrid-4-ol, and the suspension is then maintained at 70° C. for 4 hours. The resulting mixture is allowed to cool and is hydrolysed, cautiously, with sodium bicarbonate solution. The mixture is extracted with ethyl acetate. The organic phase is isolated and dried over magnesium sulfate, filtered and then concentrated under reduced pressure. 0.33 g of 4-bromo-1H-pyrazolo[4,3-c]pyrid-3-ylamine is obtained in the form of a cream-coloured solid.

Workup

  1. temperatureto cool
  2. extractionThe mixture is extracted with ethyl acetate
  3. customThe organic phase is isolated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-21e8c65997374394813aed5f8ba571f2
Source dataset
uspto-grants-2011_08
Patent number
US08008322B2

Reaction notes

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