Phenethyl bromide → HCID 22933991, compound

HRID 1269793Notes

Reaction equation

HRID 1269793 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[NH:16]1[C:24]2[C:19](=[CH:20][C:21]([OH:25])=[CH:22][CH:23]=2)[CH:18]=[N:17]1.[OH-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C(Cl)(Cl)Cl>[C:9]1([CH2:8][CH2:7][O:25][C:21]2[CH:20]=[C:19]3[C:24](=[CH:23][CH:22]=2)[NH:16][N:17]=[CH:18]3)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 1014381H-Indazol-5-ol

Product 1

HCID 22933991HCID 22933991, compoundYield 8%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (68 mg, 0.492 mmol), tetrabutylammonium iodide (17 mg, 0.0447 mmol) and phenethyl bromide (0.061 ml, 0.447 mmol) were added to a solution of the 1H-indazol-5-ol (60 mg, 0.447 mmol) obtained in Reference Example 4 in N,N-dimethylformamide (2 ml), and the resulting mixture was heated to 60° C. After 7 hours, chloroform (3 ml) and a 1M-aqueous sodium hydroxide solution (4 ml) were added to the reaction mixture and stirred. After removing the aqueous layer, water (3 ml) was added to the organic layer and stirred. After removing the aqueous layer, the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 5-(2-phenylethoxy)-1H-indazole (8.4 mg, 8%).

Workup

  1. customAfter removing the aqueous layer, water (3 ml)
  2. additionwas added to the organic layer
  3. stirringstirred
  4. customAfter removing the aqueous layer
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customThe organic layer dried
  7. concentrationwas concentrated
  8. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8641a32975384d3e8800a92ab3725685
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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