Ethyl cyanoacetate → HCID 59826886, compound

HRID 1426683Notes

Reaction equation

HRID 1426683 reaction equation
C(N(C(C)C)CC)(C)C.[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11].Br[CH:19]([CH3:29])[C:20]([C:22]1[C:23]([F:28])=[N:24][CH:25]=[CH:26][CH:27]=1)=[O:21]>O1CCCC1>[C:10]([CH:12]([CH:19]([CH3:29])[C:20]([C:22]1[C:23]([F:28])=[N:24][CH:25]=[CH:26][CH:27]=1)=[O:21])[C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 81531DiisopropylethylamineHCID 59826894HCID 59826894, compound

Product 1

HCID 59826886HCID 59826886, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of diisopropylethylamine (45 mL) and ethyl cyanoacetate (11.5 g) in tetrahydrofuran (50 mL) was added dropwise a solution of 2-bromo-1-(2-fluoropyridin-3-yl)propan-1-one (29.6 g) in tetrahydrofuran (50 mL), and the mixture was stirred at room temperature for 14 hr. Insoluble materials were filtered off, and filtrate was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=2:1) to give the title compound as a brown oil (yield 18.8 g, 85%).

Workup

  1. filtrationInsoluble materials were filtered off
  2. concentrationfiltrate was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=2:1)

Sources & evidence

ORD record
ord-4cdf080169e64dcebedb851748382553
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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