Triethylamine → HCID 66839168, compound

HRID 546735Notes

Reaction equation

HRID 546735 reaction equation
C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C(N(CC)CC)C.[C:29]([O:33][CH2:34][CH3:35])(=[O:32])[CH:30]=[CH2:31].Cl[C:37]1[N:42]=[C:41]([O:43][CH3:44])[C:40]([N+:45]([O-:47])=[O:46])=[CH:39][CH:38]=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:44][O:43][C:41]1[N:42]=[C:37](/[CH:31]=[CH:30]/[C:29]([O:33][CH2:34][CH3:35])=[O:32])[CH:38]=[CH:39][C:40]=1[N+:45]([O-:47])=[O:46]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 107977036-Chloro-2-methoxy-3-nitropyridine

Product 1

HCID 66839168HCID 66839168, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Palladium acetate (386 mg), 2-(di-tert-butylphosphino)biphenyl (1.03 g), triethylamine (9.59 mL) and ethyl acrylate (18.6 mL) were added to a solution of 6-chloro-2-methoxy-3-nitropyridine (6.49 g) in DMF (100 mL). The reaction solution was stirred in a nitrogen atmosphere at 120° C. for two hours and then left to cool to room temperature. The reaction solution was concentrated under reduced pressure. Water and ethyl acetate were added to the resulting residue, and the organic layer was separated. The resulting organic layer was washed with water and brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) and crystallized from heptane to obtain 2.1 g of the title compound. The property values of the compound are as follows.

Workup

  1. waitleft
  2. temperatureto cool to room temperature
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionWater and ethyl acetate were added to the resulting residue
  5. customthe organic layer was separated
  6. washThe resulting organic layer was washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)
  10. customcrystallized from heptane

Sources & evidence

ORD record
ord-02dcc43d65334270b5788c5ae0126634
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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