Methyl iodide → 6-Bromo-1-methyl-1H-indazole
Reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.[OH-].[K+].[CH3:13]I>CO.C(OCC)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:13])=[CH:4][CH:3]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
6-Bromoindazole (400 mg) was dissolved in methanol (10 mL). To this solution, potassium hydroxide (450 mg) was added followed by methyl iodide (0.50 mL) and the mixture was refluxed for 2.5 h. The reaction was cooled, diluted with diethyl ether, washed with water, brine, dried and concentrated. The product 6-bromo-1-methylindazole (160 mg) was separated from its isomer by Combiflash.
Workup
- temperaturethe mixture was refluxed for 2.5 h
- temperatureThe reaction was cooled
- washwashed with water, brine
- customdried
- concentrationconcentrated
- customThe product 6-bromo-1-methylindazole (160 mg) was separated from its isomer by Combiflash
Sources & evidence
- ORD record
- ord-615be3596a7d4ecc8f70f7e5d3a21df5
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637497B2
Reaction notes
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