HCID 67405279, compound → HCID 67404660, compound

HRID 910214Notes

Reaction equation

HRID 910214 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH:17]([OH:19])[CH3:18])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 67405279HCID 67405279, compound

Product 1

HCID 67404660HCID 67404660, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

Manganese dioxide (691 mg) was added to a solution of 1-[4-(6-iodoimidazo[1,2-a]pyridin-2-yl)phenyl]-1-ethanol (579 mg) in chloroform (50 mL), and the mixture was refluxed for 8 hours. The reaction mixture was filtered through Celite, and the mother liquor was concentrated. The residue was purified through silica gel column chromatography (dichloromethane:methanol=95:5), followed by concentration under reduced pressure, to thereby yield the title compound (371 mg).

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationthe mother liquor was concentrated
  4. customThe residue was purified through silica gel column chromatography (dichloromethane:methanol=95:5)
  5. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-41be382051f54f0f8cb3d7258633d0aa
Source dataset
uspto-grants-2011_09
Patent number
US08022075B2

Reaction notes

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