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

HRID 2240515Notes

Reaction equation

HRID 2240515 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-cee1e8295d9e4b999e0e3f6cac7ce064
Source dataset
uspto-grants-2010_05
Patent number
US07723349B2

Reaction notes

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