Methyl iodide → HCID 86708637, compound

HRID 921756Notes

Reaction equation

HRID 921756 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13]#[N:14])([O-:3])=[O:2].[C:15]([O-])([O-])=O.[K+].[K+].CI>CC(N(C)C)=O>[CH3:15][N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[C:7]([C:13]#[N:14])=[N:8]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 225672195-Nitro-1H-indazole-3-carbonitrile

Product 1

HCID 86708637HCID 86708637, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

5-nitro-1H-indazole-3-carbonitrile (150 mg, 0.797 mmol) was taken up in DMA (4 mL) and K2CO3 (331 mg, 2.392 mmol) was added, followed by drop wise addition of MeI (0.060 mL, 0.957 mmol). The reaction was stirred at room temperature overnight. The reaction mixture was quenched with a saturated solution of NaHCO3 and Na2S2O3, and then diluted with EtOAc. The organic layer was washed with saturated NaHCO3, then brine, and dried over Na2SO4, filtered, and concentrated. The material was purified by flash column chromatography eluting with 0%-50% EtOAc/Hex. 1-methyl-5-nitro-1H-indazole-3-carbonitrile (134 mg) was obtained as a yellow solid.

Workup

  1. customThe reaction mixture was quenched with a saturated solution of NaHCO3 and Na2S2O3
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with saturated NaHCO3
  4. dry with materialbrine, and dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified by flash column chromatography
  8. washeluting with 0%-50% EtOAc/Hex

Sources & evidence

ORD record
ord-56f97cf6a20646e68dfb562288829536
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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