Methyl iodide → 1-Methyl-1h-indazole-3-carbonitrile

HRID 549066

Reaction equation

HRID 549066 reaction equation
[H-].[Na+].[C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][N:6]=1)#[N:4].[CH3:14]I>CN(C)C=O>[C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH3:14])[N:6]=1)#[N:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 4375561H-Indazole-3-carbonitrile

Product 1

HCID 2847001-Methyl-1h-indazole-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.37 g, 60% dispersion in mineral oil) was added to a solution of 3-cyano-1H-indazole (1.20 g, Reference Example 57) in dry dimethylformamide (30 mL) under a nitrogen atmosphere at ambient temperature. The mixture was allowed to stir for 1 hour then treated with methyl iodide (0.85 mL) and stirring was continued for 1 hour. The reaction mixture was then poured into ice-water (15 mL). The precipitated solid was filtered then washed with water and then dried to give the title compound (0.80 g) as a beige solid, m.p. 73° C. 1H NMR [(CD3)2SO]: δ 7.91 (m, 2H); 7.60 (t, 1H); 7.42 (t, 1H); 4.21 (s, 3H).

Workup

  1. stirringstirring
  2. waitwas continued for 1 hour
  3. filtrationThe precipitated solid was filtered
  4. washthen washed with water
  5. customdried

Sources & evidence

ORD record
ord-36ea6e95feea47b093279056759e9ad9
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Linked notes

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