Water → HCID 90308704, compound

HRID 2283697Notes

Reaction equation

HRID 2283697 reaction equation
[H-].[Na+].I[CH2:4][CH3:5].[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[C:14]([CH3:16])[CH:15]=1)[NH:12][N:11]=[CH:10]2.O>CN(C=O)C>[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[C:14]([CH3:16])[CH:15]=1)[N:12]([CH2:4][CH3:5])[N:11]=[CH:10]2.[Br:6][C:7]1[CH:15]=[C:14]([CH3:16])[C:13]2[C:9](=[CH:10][N:11]([CH2:4][CH3:5])[N:12]=2)[CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 13820335-Bromo-7-methyl-1H-indazole

Product 2

HCID 90308704HCID 90308704, compoundHCID 90308755HCID 90308755, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil, 240 mg) and iodoethane (0.64 mL) were added to a solution of 5-bromo-7-methyl-1H-indazole (844 mg) in DMF (10 mL), and the reaction solution was stirred at room temperature for 15 minutes. Water was added to the reaction solution, and then the reaction solution was extracted with ethyl acetate. The organic layer was washed successively with water and 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 5-bromo-1-ethyl-7-methyl-1H-indazole and 5-bromo-2-ethyl-7-methyl-2H-indazole.

Workup

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. washThe organic layer was washed successively with water
  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-2129e7c1954b4681a67ad521d4fe0de7
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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