Methyl iodide → 6-Bromo-1-methyl-1H-indazole

HRID 1664628

Reaction equation

HRID 1664628 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]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 178424716-Bromo-1H-indazole

Product 1

HCID 225586756-Bromo-1-methyl-1H-indazole

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

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

  1. temperaturethe mixture was refluxed for 2.5 h
  2. temperatureThe reaction was cooled
  3. washwashed with water, brine
  4. customdried
  5. concentrationconcentrated
  6. customThe product 6-bromo-1-methylindazole (160 mg) was separated from its isomer by Combiflash

Sources & evidence

ORD record
ord-f391e8ec558c4f93a563fe826edb395a
Source dataset
uspto-grants-2011_10
Patent number
US08039471B2

Linked notes

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