Isopropyl iodide → HCID 12991242, compound

HRID 2084049Notes

Reaction equation

HRID 2084049 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][NH:10]2)=[CH:6][CH:5]=1.I[CH:14]([CH3:16])[CH3:15]>CN(C=O)C>[I:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH:14]([CH3:16])[CH3:15])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 129912416-iodo-1H-indazole

Product 1

HCID 12991242HCID 12991242, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (85 mg, 60%, 2.12 mmol) was added to an ice-cooled solution of 6-iodo-1H-indazole (249.5 mg, 1.02 mmol) in DMF (2.5 mL). After stirring this mixture for 1 h at 0° C., 2-iodopropane (0.32 mL, 3.2 mmol) was added and the mixture stirred at 100° C. for 16 h. After the reaction mixture was partitioned between water and ethyl acetate, the organic layer was washed sequentially with water and brine, dried over sodium sulfate and the solvent removed in vacuo. Flash chromatography (silica gel, 5-20% ethyl acetate in hexane) yielded two products, the less polar 1-substituted-1H-indazole (105 mg) and the more polar 2-substituted indazolium (107.7 mg).

Workup

  1. stirringthe mixture stirred at 100° C. for 16 h
  2. customAfter the reaction mixture was partitioned between water and ethyl acetate
  3. washthe organic layer was washed sequentially with water and brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed in vacuo
  6. customFlash chromatography (silica gel, 5-20% ethyl acetate in hexane) yielded two products

Sources & evidence

ORD record
ord-5c486260b9274028873499ca7d8046b2
Source dataset
uspto-grants-2004_04
Patent number
US06716837B1

Reaction notes

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