Sodium hydride → HCID 86693020, compound

HRID 1502134Notes

Reaction equation

HRID 1502134 reaction equation
[H-].[Na+].[C:3]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:17]1[C:18]([CH3:26])=[N:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=1>CN(C=O)C>[CH3:26][C:18]1[C:17]([CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])=[CH:22][CH:21]=[C:20]([N+:23]([O-:25])=[O:24])[N:19]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 96345tert-Butyl ethyl malonateHCID 58939295HCID 58939295, compound

Product 1

HCID 86693020HCID 86693020, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

To a suspension of NaH (60% in oil, 1.4 g, 36 mmol)) in DMF (50 mL) was added tert-butyl ethyl propanedioate (6.8 g, 36 mmol) at room temperature. The mixture was stirred for 30 min. A solution of 3-chloro-2-methyl-6-nitropyridine (4.8 g, 28 mmol) in DMF (10 mL) was added. The mixture was heated to 80° C. and stirred for 5 h. Cooled to ambient temperature, poured to ice/water, extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated and the residue was purified by column chromatography to give title compound.

Workup

  1. stirringstirred for 5 h
  2. temperatureCooled to ambient temperature
  3. extractionextracted with EtOAc
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-7016529e929c4eaaa33ec435824ac8da
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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