Ethyl cyanoacetate → HCID 49788127, compound

HRID 2383004Notes

Reaction equation

HRID 2383004 reaction equation
[Na].[CH2:2]([O:4][C:5](=[O:9])[CH2:6][C:7]#[N:8])[CH3:3].Br.Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)=[O:14].CCN(C(C)C)C(C)C>CCO.C1COCC1>[CH2:2]([O:4][C:5](=[O:9])[CH:6]([C:7]#[N:8])[CH2:12][C:13](=[O:14])[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[CH3:3]

Participants

7

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 81531DiisopropylethylamineHCID 27762394-(Bromoacetyl)pyridine hydrobromideHCID 5360545Sodium2×

Product 1

HCID 49788127HCID 49788127, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium metal (81 mg, 3.5 mmol) in 10 mL anhydrous EtOH, ethylcyanoacetate (0.37 mL, 3.5 mmol) was added at 0° C. The solution was stirred until sodium was completely dissolved. The solvent was evaporated to obtain a white solid that was added portionwise to a stirred solution of bromoacetylpyridine 1 (1.0 g, 3.5 mmol) in anhydrous THF (20 mL) and DIEA (0.6 mL, 3.5 mmol). The reaction mixture was stirred overnight at rt. The solvent was removed, the residue was suspended in water and extracted with DCM. The organic extracts were dried over Na2SO4 and concentrated. The crude was purified by flash chromatography (DCM/MeOH 95:5) to give 710 mg (87%) of 2-cyano-4-oxo-4-pyridin-4-yl-butyric acid ethyl ester as a reddish oil.

Workup

  1. additionwas added at 0° C
  2. dissolutionwas completely dissolved
  3. customThe solvent was evaporated
  4. customto obtain a white solid
  5. customThe solvent was removed
  6. extractionextracted with DCM
  7. dry with materialThe organic extracts were dried over Na2SO4
  8. concentrationconcentrated
  9. customThe crude was purified by flash chromatography (DCM/MeOH 95:5)

Sources & evidence

ORD record
ord-f03038c6706044e3a4876a13989c9b0a
Source dataset
uspto-grants-2012_09
Patent number
US08263604B2

Reaction notes

Loading…