Methyl iodide → 2-Methyl-2H-indazole-7-carbonitrile

HRID 2203195Notes

Reaction equation

HRID 2203195 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]#[N:11])[CH:3]=[N:2]1.[C:12]([O-])([O-])=O.[Cs+].[Cs+].CI>C(#N)C>[CH3:12][N:2]1[CH:3]=[C:4]2[C:9]([C:8]([C:10]#[N:11])=[CH:7][CH:6]=[CH:5]2)=[N:1]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 250226851H-Indazole-7-carbonitrile

Product 1

HCID 441192602-Methyl-2H-indazole-7-carbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1H-indazole-7-carbonitrile (1 equiv.) in acetonitrile, Cs2CO3 (1.3 equiv.) and MeI (3 equiv.) was added and reaction was heated at 80° C. for 1.5 h. On completion, it was cooled and quenched by addition of water. Extraction was carried out using ethyl acetate. Organic layer was dried over Na2SO4 and crude compound was column purified to afford the title compound. (Polar isomer confirmed as N-2-Methyl and non-polar isomer confirmed as N-1-Methyl by NOE experimentation).

Workup

  1. customreaction
  2. temperatureOn completion, it was cooled
  3. customquenched by addition of water
  4. extractionExtraction
  5. dry with materialOrganic layer was dried over Na2SO4 and crude compound
  6. custompurified

Sources & evidence

ORD record
ord-f56d179d4ab64601ab87fd59d5c0b195
Source dataset
uspto-grants-2016_06
Patent number
US09365570B2

Reaction notes

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