Hydrogen Bromide → HCID 67207447, compound

HRID 1253539Notes

Reaction equation

HRID 1253539 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:11]C)[C:5]2[N:6]([N:8]=[CH:9][CH:10]=2)[CH:7]=1.Br.[OH-].[Na+]>O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5]2[N:6]([N:8]=[CH:9][CH:10]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 446228256-Bromo-4-methoxypyrazolo[1,5-a]pyridine

Product 1

HCID 67207447HCID 67207447, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

6-bromo-4-methoxypyrazolo[1,5-a]pyridine (1.50 g, 6.61 mmol) was suspended in HBr (15 ml, 133 mmol). The reaction mixture was heated in the Biotage Initiator Series microwave for 80 minutes at 150° C. The reaction mixture was added dropwise via pipette to a mixture of NaOH (5.29 g, 132 mmol) in 50 mL of water and ice. The mixture was diluted in ethyl acetate, washed with saturated aqueous sodium bicarbonate and brine then dried over sodium sulfate, filtered and concentrated to give 6-bromopyrazolo[1,5-a]pyridin-4-ol.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate and brine
  2. dry with materialthen dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f7583cc29d5647949bc680136988c357
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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