Styrene → HCID 67047630, compound

HRID 606837Notes

Reaction equation

HRID 606837 reaction equation
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.Br[C:31]1[CH:32]=[N:33][CH:34]=[C:35]([CH:38]=1)[C:36]#[N:37].[CH2:39]=[CH:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CN(C)C=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH:39](/[C:31]1[CH:32]=[N:33][CH:34]=[C:35]([CH:38]=1)[C:36]#[N:37])=[CH:40]\[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

8

Reactant 4

HCID 7501StyreneHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 7367935-Bromonicotinonitrile

Product 1

HCID 67047630HCID 67047630, compoundYield 34%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Add tris(dibenzylideneacetone)dipalladium (125 mg, 0.136 mmol) and tri-o-tolylphosphine (86 mg, 0.273 mmol) to a solution of triethylamine (0.77 mL, 5.46 mmol), 5-bromonicotinonitrile (500 mg, 2.73 mmol) and styrene (0.48 mL, 4.1 mmol) in anhydrous N,N-dimethylformamide (10 mL) under an inert atmosphere, and stir at 100° C. for 3.5 h. Cool to room temperature, add water and extract three times with diethyl ether. Combine the organic layers, dry (sodium sulfate), filter, and concentrate. Purify the residue by silica gel chromatography, eluting with dichloromethane, to give the title compound as a white solid (190 mg, 34%).

Workup

  1. temperatureCool to room temperature
  2. extractionextract three times with diethyl ether
  3. dry with materialdry (sodium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the residue by silica gel chromatography
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-8324edd1a6c843be92bdf6e9067462be
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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