Methylhydrazine → 4-Bromo-1-methyl-1H-indazole
Reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6](F)[C:3]=1[CH:4]=O.[CH3:11][NH:12][NH2:13]>CS(C)=O.O>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:3]=1[CH:4]=[N:13][N:12]2[CH3:11]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 85 °C
Procedure
The product of Example 2B (2.0 g) was dissolved in DMSO (2 g) and the solution was added to methylhydrazine (98%, 3.2 g, 7 eq.). The mixture was heated for 24 hours at 85° C., cooled to ambient temperature and diluted with water (50 mL). The solution was extracted with CH2Cl2 (2×50 mL) and the combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to provide the title compound.
Workup
- temperaturecooled to ambient temperature
- extractionThe solution was extracted with CH2Cl2 (2×50 mL)
- dry with materialthe combined organic layers were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-b9412e38774b4a03b0233006797d5253
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815930B2
Reaction notes
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