Iodine → HCID 178440467, compound

HRID 14501Notes

Reaction equation

HRID 14501 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:24])[C:10]3[C:11]([O:19][C:20]=2[CH:21]([CH3:23])[CH3:22])=[C:12]2[C:16](=[CH:17][CH:18]=3)[NH:15][N:14]=[CH:13]2)=[CH:4][CH:3]=1.[OH-].[K+].[I:27]I>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9](=[O:24])[C:10]3[C:11]([O:19][C:20]=2[CH:21]([CH3:22])[CH3:23])=[C:12]2[C:16](=[CH:17][CH:18]=3)[NH:15][N:14]=[C:13]2[I:27])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 687032613-(4-Chlorophenyl)-2-isopropyl-7H-pyrano[2,3-e]indazol-4-one

Product 1

HCID 178440467HCID 178440467, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(4-chlorophenyl)-2-isopropyl-7H-pyrano[2,3-e]indazol-4-one (20 mg, 0.059 mmol) in dry N,N-dimethylformamide (2 ml) at room temperature are added potassium hydroxide (6.3 mg, 0.112 mmol) and iodine (55 mg, in three portions over 3 h, 0.217 mmol). The reaction mixture is stirred at room temperature for 20 h, then diluted with ethyl acetate and washed successively with 10% aqueous sodium thiosulfate solution (40 ml) and saturated brine (40 ml). The organic phase is dried (MgSO4), filtered and evaporated under reduced pressure. The resulting solid is triturated with n-hexane/dichloromethane to give a colourless solid that is recovered by filtration and dried.

Workup

  1. washwashed successively with 10% aqueous sodium thiosulfate solution (40 ml) and saturated brine (40 ml)
  2. dry with materialThe organic phase is dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe resulting solid is triturated with n-hexane/dichloromethane
  6. customto give a colourless solid that
  7. filtrationis recovered by filtration
  8. customdried

Sources & evidence

ORD record
ord-008d1b1039134b6bb27ddee169105178
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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