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

HRID 2167683Notes

Reaction equation

HRID 2167683 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

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 oC 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. temperaturewas heated at 80 oC for 1.5 h
  3. temperatureOn completion, it was cooled
  4. customquenched by addition of water
  5. extractionExtraction
  6. dry with materialOrganic layer was dried over Na2SO4 and crude compound
  7. custompurified

Sources & evidence

ORD record
ord-1b9d0df2249c4119be46a854613f7786
Source dataset
uspto-grants-2015_06
Patent number
US09045477B2

Reaction notes

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