Hydrogen Bromide → HCID 67373747, compound
Reaction equation
[Br:1][C:2]1[C:3]2[N:4]([N:10]=[CH:11][CH:12]=2)[CH:5]=[C:6]([O:8]C)[CH:7]=1.Br.[OH-].[Na+]>C(=O)(O)[O-].[Na+].C(OCC)(=O)C>[Br:1][C:2]1[C:3]2[N:4]([N:10]=[CH:11][CH:12]=2)[CH:5]=[C:6]([OH:8])[CH:7]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 150 °C
Procedure
4-bromo-6-methoxypyrazolo[1,5-a]pyridine (725 mg, 3.19 mmol) was suspended in HBr (12 ml, 106 mmol). The reaction mixture was heated in the Biotage Initiator Series microwave for 1 h at 150° C. The reaction mixture was slowly added via pipete to a solution of 5N NaOH (22.0 ml, 110 mmol) in 100 mL of saturated aqueous sodium bicarbonate at 0° C. The reaction mixture was diluted in ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and brine then dried over sodium sulfate, filtered and concentrated to afford 4-bromopyrazolo[1,5-a]pyridin-6-ol.
Workup
- washwashed with saturated aqueous sodium hydrogen carbonate and brine
- dry with materialthen dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9c01736c24a4484699a398f01b97a0eb
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08455477B2
Reaction notes
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