Hydrogen Bromide → 5-Bromo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazole
Reaction equation
[N:1]1([CH2:6][CH2:7][N:8]2[C:16]3[C:11](=[CH:12][C:13](N)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.N([O-])=O.[Na+].[BrH:22]>O>[Br:22][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([CH2:7][CH2:6][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[N:9]=[CH:10]2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
1.00 g (4.34 mmol) 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-ylamine is dissolved in 9.76 mL 48% hydrobromic acid and 9.76 mL water and the solution is cooled to 0° C. 2.5 M sodium nitrite solution (300 mg in 1.74 mL water) is slowly added dropwise. The reaction is stirred for 10 min at 0° C. and then a solution of 935 mg (6.51 mmol) CuBr in 3.42 mL 48% hydrobromic acid is added dropwise. The reaction is heated to 60° C. and stirred for one hour at this temperature. The mixture is diluted with water and the aqueous phase is extracted with EtOAc. The organic phase is discarded and the aqueous phase is made alkaline with saturated NaHCO3 solution. The aqueous phase is extracted with EtOAc and the organic phase is washed with water. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac.
Workup
- temperatureThe reaction is heated to 60° C.
- stirringstirred for one hour at this temperature
- extractionthe aqueous phase is extracted with EtOAc
- extractionThe aqueous phase is extracted with EtOAc
- washthe organic phase is washed with water
- dry with materialThe organic phase is dried over MgSO4
Sources & evidence
- ORD record
- ord-ef632ad3988e451b9e13730e5e70c898
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618132B2
Reaction notes
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