Iodoethane → 5-Ethoxy-1H-indazole

HRID 2064666Notes

Reaction equation

HRID 2064666 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.C(=O)([O-])[O-].[K+].[K+].I[CH2:18][CH3:19].C(OCC)(=O)C>CC(C)=O.CCCCCC>[CH2:18]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2)[CH3:19]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1014381H-Indazol-5-ol

Product 1

HCID 220559665-Ethoxy-1H-indazole

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8058HexaneSolvent

Procedure

A solution of 5-hydroxy-1H-indazole [0.5 g, Reference Example 38] in acetone (10 ml) was treated with potassium carbonate (2.56 g) then with iodoethane (0.296 ml). The mixture was refluxed for 4 hours then cooled and then evaporated. The residue was partitioned between ethyl acetate and water and the aqueous layer was further extracted twice with ethyl acetate. The combined organic fractions were dried over magnesium sulfate and then evaporated to yield a brown residue which was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and hexane (1:1, v/v) to give 5-ethoxy-1H-indazole (0.38 g) as an off-white solid. LC-MS (METHOD B): RT=2.68 minutes; 163 (M+H)+.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. temperaturethen cooled
  3. customevaporated
  4. customThe residue was partitioned between ethyl acetate and water
  5. extractionthe aqueous layer was further extracted twice with ethyl acetate
  6. dry with materialThe combined organic fractions were dried over magnesium sulfate
  7. customevaporated
  8. customto yield a brown residue which

Sources & evidence

ORD record
ord-d28c98cad975412691c3b53f70d8e294
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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