Iodine → HCID 178506570, compound

HRID 1726046Notes

Reaction equation

HRID 1726046 reaction equation
[I:1]I.[OH-].[K+].[CH2:5]([O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18](C(=O)C)[N:17]=[CH:16]2)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O.ClCCl.C(OCC)(=O)C.O>[CH2:5]([O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][N:17]=[C:16]2[I:1])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

9

Reactant 4

HCID 807IodineHCID 14797Potassium Hydroxide2×HCID 24477Sodium ThiosulfateHCID 225672491-(5-(Benzyloxy)-1H-indazol-1-yl)ethan-1-one

Product 1

HCID 178506570HCID 178506570, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

68.84 g of iodine and then 23 g of potassium hydroxide are added to a solution of 28.24 g of 1-(5-benzyloxyindazol-1-yl)ethanone in 620 ml of dimethylformamide. The reaction medium is stirred at ambient temperature for approximately 3 hours. 23 g of potassium hydroxide are added and the medium is stirred at ambient temperature for 48 hours. The medium is treated with 600 ml of a sodium thiosulfate solution (100 g of sodium thiosulfate in 250 ml of distilled water), 600 ml of distilled water and 1 liter of ethyl acetate. The medium is stirred for a few minutes and is then separated by settling out. The aqueous phase is extracted with 4×600 ml of ethyl acetate. The combined organic phases are washed with 1 liter of a saturated sodium chloride solution, and then dried over magnesium sulfate. The solvent is evaporated off under reduced pressure in a rotary evaporator. The reaction crude is taken up in dichloromethane, and the solid is filtered off and rinsed with dichloromethane and with ethyl ether. 20.8 g of 5-benzyloxy-3-iodo-1H-indazole are collected.

Workup

  1. stirringthe medium is stirred at ambient temperature for 48 hours
  2. stirringThe medium is stirred for a few minutes
  3. customis then separated
  4. extractionThe aqueous phase is extracted with 4×600 ml of ethyl acetate
  5. washThe combined organic phases are washed with 1 liter of a saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent is evaporated off under reduced pressure in a rotary evaporator
  8. customThe reaction crude
  9. filtrationthe solid is filtered off
  10. washrinsed with dichloromethane and with ethyl ether
  11. custom20.8 g of 5-benzyloxy-3-iodo-1H-indazole are collected

Sources & evidence

ORD record
ord-3cce9192967b411c8ba3e6e319be65ab
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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