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

HRID 1257512Notes

Reaction equation

HRID 1257512 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, compoundYield 99.7%

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 (33.7 g).

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-f0bd1cf5e18d4a83b76878728de5f1a2
Source dataset
uspto-grants-2013_06
Patent number
US08461185B2

Reaction notes

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