Sodium Thiosulfate → HCID 59631569, compound

HRID 1431758Notes

Reaction equation

HRID 1431758 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH:19]=C)=[C:7]([CH3:18])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1.C[N+]1([O-])CC[O:25]CC1.S([O-])([O-])(=O)=S.[Na+].[Na+].I([O-])(=O)(=O)=O.[Na+]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH:19]=[O:25])=[C:7]([CH3:18])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 59631216HCID 59631216, compound

Product 1

HCID 59631569HCID 59631569, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 7-fluoro-3-methyl-2-(pyridin-2-yl)-4-vinylquinoline (1.53 g, 5.79 mmol) in acetone (30 mL) and water (7.50 mL) were added N-methylmorpholine-N-oxide (2.034 g, 17.37 mmol) and osmium tetroxide (0.074 g, 0.289 mmol). The reaction was stirred at 23° C. for 18 h. Upon completion, 10% aqueous sodium thiosulfate was added and the reaction was stirred for an additional 10 minutes. The reaction mixture was then concd, and the dihydroxylated product was extracted with EtOAc (twice) and DCM (twice). The combined organics were dried over magnesium sulfate and concd, and the resulting residue was resolubilized in 30 mL 4:1 acetone:water and 3 mL dioxane. To this solution sodium periodate (3.10 g, 14.47 mmol) was added, and stirring continued at 23° C. for 2 h. Upon completion, the organic solvents were removed under vacuum, and the afforded crude material was partitioned between EtOAc and water. The organic phase was dried over magnesium sulfate and concd, and purification by column chromatography (silica; 0-70% EtOAc in hexanes yielded 7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline-4-carbaldehyde as a white amorphous solid. Mass Spectrum (ESI) m/e=367.1 (M+1).

Workup

  1. stirringthe reaction was stirred for an additional 10 minutes
  2. extractionthe dihydroxylated product was extracted with EtOAc (twice) and DCM (twice)
  3. dry with materialThe combined organics were dried over magnesium sulfate and concd
  4. stirringstirring
  5. waitcontinued at 23° C. for 2 h
  6. customUpon completion, the organic solvents were removed under vacuum
  7. customthe afforded crude material
  8. customwas partitioned between EtOAc and water
  9. dry with materialThe organic phase was dried over magnesium sulfate and concd, and purification by column chromatography (silica

Sources & evidence

ORD record
ord-e90ff463049e4e11b5fcc1759f72c16e
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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