Diethyl Malonate → HCID 67008743, compound

HRID 2390257Notes

Reaction equation

HRID 2390257 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])[CH:5]=[N:6][C:7]=1Cl.[C:15]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].[H-].[Na+]>C1COCC1>[Br:1][C:2]1[C:7]([CH:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:15]([O:23][CH2:24][CH3:25])=[O:22])=[N:6][CH:5]=[C:4]([S:9]([N:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 4730021HCID 4730021, compound

Product 1

HCID 67008743HCID 67008743, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-bromo-6-chloro-N,N-dimethylpyridine-3-sulfonamide (400 mg; 1.34 mmol) and diethyl malonate (204 μl; 1.34 mmol) in anhydrous THF (2 ml) was added to a suspension of sodium hydride (53 mg; 1.34 mmol) in anhydrous THF (2 ml). The resulting mixture was stirred for 48 hours, then quenched by careful addition of a saturated solution of NH4Cl in water. EtOAc was added and the phases separated. The organic phase was washed with brine, dried on MgSO4, filtered and concentrated under reduced pressure to give a residue which was purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc to give the title compound as a colorless oil.

Workup

  1. customquenched by careful addition of a saturated solution of NH4Cl in water
  2. additionEtOAc was added
  3. customthe phases separated
  4. washThe organic phase was washed with brine
  5. customdried on MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a residue which
  9. customwas purified by flash column chromatography (silica)
  10. washeluting with cyclohexane containing
  11. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-7ded80cbafdf4f618e8812ecd5ec275e
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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