Hydrogen Peroxide → 2-(2,6-Dichloro-4-iodophenyl)-7-fluorothiazolo[5,4-c]pyridine-5-oxide

HRID 2366317Notes

Reaction equation

HRID 2366317 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[C:10]1[S:11][C:12]2[CH:13]=[N:14][CH:15]=[C:16]([F:19])[C:17]=2[N:18]=1.[OH:20]O>C(Cl)Cl.C[Re](=O)(=O)=O>[Cl:9][C:4]1[CH:5]=[C:6]([I:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[C:10]1[S:11][C:12]2[CH:13]=[N+:14]([O-:20])[CH:15]=[C:16]([F:19])[C:17]=2[N:18]=1

Participants

5

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 668015632-(2,6-Dichloro-4-iodophenyl)-7-fluorothiazolo[5,4-c]pyridine

Product 1

HCID 668013882-(2,6-Dichloro-4-iodophenyl)-7-fluorothiazolo[5,4-c]pyridine-5-oxideYield 45%

Reagents, catalysts & solvents 2

HCID 178477782HCID 178477782, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2,6-dichloro-4-iodophenyl)-7-fluorothiazolo[5,4-c]pyridine (5.3 g, 12.6 mmol) in DCM (100 mL) under a nitrogen atmosphere was added methyltrioxorhenium(VII) (313 mg, 1.3 mmol) followed by 30% aqueous hydrogen peroxide (2.6 mL, 25.1 mmol). The reaction mixture was stirred at room temperature for 48 hours with a further two additions of methyltrioxorhenium(VII) (313 mg, 1.3 mmol) and 30% aqueous hydrogen peroxide (2.6 mL, 25.1 mmol) added over this period. The precipitate obtained was collected by filtration and the filtrate was partitioned between water. The aqueous layer was extracted with DCM (×2). The combined organic phases were washed with a saturated solution of NaHCO3, dried (MgSO4) and concentrated under reduced pressure. The resultant residue was combined with the previously filtered solid and was purified by column chromatography on silica gel eluting with 0-90% EtOAc in petroleum ether (40-60° C.), followed by 0-10% MeOH in DCM to afford the title compound as a white solid (2.5 g, 45% yield). LCMS (Method D): RT=3.36 min, m/z: 441 [M+H+].

Workup

  1. additionadded over this period
  2. customThe precipitate obtained
  3. filtrationwas collected by filtration
  4. customthe filtrate was partitioned between water
  5. extractionThe aqueous layer was extracted with DCM (×2)
  6. washThe combined organic phases were washed with a saturated solution of NaHCO3
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. customwas purified by column chromatography on silica gel eluting with 0-90% EtOAc in petroleum ether (40-60° C.)

Sources & evidence

ORD record
ord-2fb054fcae394a21971d79b4af17e02f
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

Loading…