Methyl iodide → HCID 22472997, compound

HRID 2183743Notes

Reaction equation

HRID 2183743 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][N:15]=[CH:14]3)=[N:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:22]I>CN(C=O)C.O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:22])[N:15]=[CH:14]3)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22472992HCID 22472992, compound

Product 1

HCID 22472997HCID 22472997, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(5-Nitro-pyridin-2-yloxy)-1H-indazole (1.0 g, 3.9 mmol) in 15 mL of DMF is added sodium hydride (3.9 mmol) and methyl iodide (20 mmol). The resulting mixture is stirred at room temperature to 50° C. for 1-6 hours. The mixture is diluted with water, extracted 3× with ethyl acetate, and the combined organic layers are dried over sodium sulfate, filtered and concentrated in vacuo. Purification by column chromatography eluting with ethyl acetate-hexanes, affords 5-(5-Nitro-pyridin-2-yloxy)-1-methyl-1H-indazole.

Workup

  1. extractionextracted 3× with ethyl acetate
  2. dry with materialthe combined organic layers are dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography
  6. washeluting with ethyl acetate-hexanes

Sources & evidence

ORD record
ord-f0e6a9605f70447ab3cdf81c0e9dc974
Source dataset
uspto-grants-2005_05
Patent number
US06900201B2

Reaction notes

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