Potassium hydroxy sulfite → HCID 68992412, compound

HRID 1930090Notes

Reaction equation

HRID 1930090 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[N:15]([C:16]=1[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([S:23][CH3:24])[N:18]=1)[CH:14]=[CH:13][O:12]2.[OH:25]OS([O-])=O.[K+]>CO.C(Cl)Cl.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[N:15]([C:16]=1[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([S:23]([CH3:24])=[O:25])[N:18]=1)[CH:14]=[CH:13][O:12]2

Participants

6

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 68993424HCID 68993424, compound

Product 1

HCID 68992412HCID 68992412, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A round bottom flask was charged with 6-(2,4-difluorophenyl)-5-(2-(methylthio)pyrimidin-4-yl)imidazo[2,1-b]oxazole (0.16 g, 0.47 mmol) and OXONE® (0.312 g, 0.508 mmol). The reaction mixture was diluted with MeOH (10.0 mL), DCM (10.0 mL) and water (2.0 mL). The reaction mixture was stirred at ambient temperature for about 8 h. The reaction mixture was quenched with water (100 mL) and extracted with DCM (2×200 mL). The organic phase was washed with H2O (100 mL) then dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography using a gradient of 10-100% EtOAc in heptane and then a gradient of 0-20% MeOH in DCM to give the title compound (0.16 g, 96%). LC/MS (Table 1, Method o) Rt=2.63 min; MS m/z 361.1.

Workup

  1. customThe reaction mixture was quenched with water (100 mL)
  2. extractionextracted with DCM (2×200 mL)
  3. washThe organic phase was washed with H2O (100 mL)
  4. dry with materialthen dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-7ab23b07b3a34d27becb16e72f94f3ea
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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