Iodoethane → HCID 90308741, compound

HRID 2283711Notes

Reaction equation

HRID 2283711 reaction equation
I[CH2:2][CH3:3].[H-].[Na+].[CH3:6][C:7]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[C:12]2[C:8]=1[CH:9]=[N:10][NH:11]2>CN(C=O)C>[CH2:2]([N:11]1[C:12]2[C:8](=[C:7]([CH3:6])[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=2)[CH:9]=[N:10]1)[CH3:3].[CH2:2]([N:10]1[CH:9]=[C:8]2[C:12]([CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=[C:7]2[CH3:6])=[N:11]1)[CH3:3]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 24728762HCID 24728762, compound

Product 2

HCID 90308741HCID 90308741, compoundHCID 90308781HCID 90308781, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodoethane (1.2 mL) and sodium hydride (60% in oil; 600 mg) were added to a solution of 4-methyl-6-nitro-1H-indazole (1.77 g), which can be synthesized by the method described in Patent No. WO 2009/084695, in DMF (17 mL), and the reaction solution was stirred at room temperature for 15 minutes. After dilution with ethyl acetate, the reaction solution was washed with water twice and then with a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain 1-ethyl-4-methyl-6-nitro-1H-indazole and 2-ethyl-4-methyl-6-nitro-2H-indazole as a light yellow solid, respectively.

Workup

  1. customcan be synthesized by the method
  2. washAfter dilution with ethyl acetate, the reaction solution was washed with water twice
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. customthe solvent was evaporated under vacuum
  5. customThe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8f5627b29a36422aaf50f0c5ba8868c3
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

Loading…