3-Methylpyridine-2-carboxaldehyde → HCID 89310361, compound

HRID 2370760Notes

Reaction equation

HRID 2370760 reaction equation
[CH3:1][C:2]1[C:3]([CH:8]=O)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:10][C:11]([S@@:14]([NH2:16])=[O:15])([CH3:13])[CH3:12]>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:10][C:11]([S@@:14](/[N:16]=[CH:8]/[C:3]1[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:15])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 15018743-Methylpyridine-2-carboxaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 89310361HCID 89310361, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methyl-2-pyridinecarboxaldehyde (3.243 g, 26.8 mmol) in DCM (18 mL) was added (S)-2-methylpropane-2-sulfinamide (6.55 g, 54.0 mmol) and copper(II) sulfate (8.72 g, 54.6 mmol). The suspension was stirred at rt for 17 hours, filtered, and the solid was washed with DCM (2×35 mL). The filtrates were concentrated, and the resulting product was purified by silica gel flash column chromatography (using a 80G ISCO cartridge) and eluted using DCM/MeOH gradient to yield the desired product (S,E)-2-methyl-N-((3-methylpyridin-2-yl)methylene)propane-2-sulfinamide as a yellow solid.

Workup

  1. filtrationfiltered
  2. washthe solid was washed with DCM (2×35 mL)
  3. concentrationThe filtrates were concentrated
  4. customthe resulting product was purified by silica gel flash column chromatography (
  5. washeluted

Sources & evidence

ORD record
ord-a1b960a92a014684a22ada3c52bfb436
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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