5-Fluoropyridine-2-carboxaldehyde → HCID 87094779, compound

HRID 888343Notes

Reaction equation

HRID 888343 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=O)=[N:6][CH:7]=1.[CH3:10][C:11]([S@:14]([NH2:16])=[O:15])([CH3:13])[CH3:12]>C(OCC)(=O)C.C1COCC1.S([O-])([O-])(=O)=O.[Cu+2]>[F:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[N:16]/[S:14]([C:11]([CH3:13])([CH3:12])[CH3:10])=[O:15])=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 103516975-Fluoropyridine-2-carboxaldehydeHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 87094779HCID 87094779, compound

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-fluoropyridine-2-carbaldehyde (18.49 g, 148 mmol) in ethyl acetate (850 mL), THF (250 mL) and hexanes (300 mL) were added (R)-(+)-2-methyl-2-propanesulfinamide (19.71 g, 163 mmol) and anhydrous copper(II) sulfate (59.0 g, 370 mmol). The mixture was stirred at ambient temperature. After 18 h, the mixture was filtered through Celite. The filtered cake was washed with ethyl acetate and the filtrate was concentrated. Purification by silica gel chromatography (100% dichloromethane→98% dichloromethane/methanol) gave the title compound.

Workup

  1. filtrationthe mixture was filtered through Celite
  2. washThe filtered cake was washed with ethyl acetate
  3. concentrationthe filtrate was concentrated
  4. customPurification by silica gel chromatography (100% dichloromethane→98% dichloromethane/methanol)

Sources & evidence

ORD record
ord-fa0e7f323fce46a1b3d035713c8a812c
Source dataset
uspto-grants-2012_08
Patent number
US08247401B2

Reaction notes

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