3-methoxypyridine-2-carbaldehyde → HCID 89310480, compound

HRID 509319Notes

Reaction equation

HRID 509319 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH:9]=O)=[N:5][CH:6]=[CH:7][CH:8]=1.[CH3:11][C:12]([S@@:15]([NH2:17])=[O:16])([CH3:14])[CH3:13]>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:1][O:2][C:3]1[C:4](/[CH:9]=[N:17]/[S@:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 53247723-methoxypyridine-2-carbaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 89310480HCID 89310480, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methoxy-pyridine-2-carbaldehyde (2.95 g, 21.51 mmol) in DCM (26 mL) was added (S)-2-methylpropane-2-sulfinamide (5.3 g, 43.7 mmol) and copper(II) sulfate (6.95 g, 43.5 mmol). The suspension was stirred at rt under argon for 18 hours, filtered, and the solid washed with DCM (2×20 mL). The filtrates were concentrated, and the product thus obtained was purified by silica gel flash column chromatography (using a 80G ISCO cartridge) and eluted using hexanes/EtOAc gradient followed by DCM/MeOH to yield the desired product (S,E)-N-((3-methoxypyridin-2-yl)methylene)-2-methylpropane-2-sulfinamide as a light-yellow solid after drying under high vacuum.

Workup

  1. filtrationfiltered
  2. washthe solid washed with DCM (2×20 mL)
  3. concentrationThe filtrates were concentrated
  4. customthe product thus obtained
  5. customwas purified by silica gel flash column chromatography (
  6. washeluted

Sources & evidence

ORD record
ord-5b2eb6c49e2f4b898a37b61f2f32af34
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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