Water → HCID 67463862, compound

HRID 553869Notes

Reaction equation

HRID 553869 reaction equation
C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N.Br[CH2:27][CH2:28][C:29]([N:31]1[CH:36]=[CH:35][C:34](=[O:37])[CH2:33][CH:32]1[C:38]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=1)=[O:30].O>C1C=CC=CC=1>[F:44][C:41]1[CH:42]=[CH:43][C:38]([CH:32]2[CH2:33][C:34](=[O:37])[CH2:35][CH:36]3[N:31]2[C:29](=[O:30])[CH2:28][CH2:27]3)=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 67461671HCID 67461671, compound

Product 1

HCID 67463862HCID 67463862, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of tributyltin hydride (3.88 mL) and 2,2′-azobis(isobutyronitrile) (0.56 g) in benzene (25 mL) was added dropwise to a solution of 1-(3-bromopropionyl)-2-(4-fluorophenyl)-2,3-dihydro-1H-pyridin-4-one obtained above (2.9 g) in benzene (60 mL) at 90° C. over four hours. The reaction solution was stirred at the same temperature for three hours. The reaction solution was returned to room temperature and poured into water, followed by extraction with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate system) to obtain 600 mg of the title compound. The property values of the compound are as follows.

Workup

  1. customwas returned to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-0345054455074382a2205133449c508f
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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