Iodoethane → 5-Ethoxy-1H-indazole

HRID 2170745Notes

Reaction equation

HRID 2170745 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[CH2:11](I)[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:11]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2)[CH3:12]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 1014381H-Indazol-5-ol

Product 1

HCID 220559665-Ethoxy-1H-indazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-hydroxyindazole (2.68 g) in DMF (50 mL) were added ethyl iodide (3.28 g) and potassium carbonate (4.16 g), and the mixture was stirred at room temperature for 1 day. Then, the mixture was partitioned between ethyl acetate and water, the organic layer was washed with brine and dried over Na2SO4, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate as the eluting solvent) to give Compound Q9 (1.95 g).

Workup

  1. customThen, the mixture was partitioned between ethyl acetate and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate as the eluting solvent)
  6. customto give Compound Q9 (1.95 g)

Sources & evidence

ORD record
ord-0fa0bd6698114d01ac59dab4e3163fdb
Source dataset
uspto-grants-2015_06
Patent number
US09051295B2

Reaction notes

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