Acrylonitrile → HCID 57072243, compound

HRID 448514Notes

Reaction equation

HRID 448514 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.I[C:28]1[CH:29]=[CH:30][C:31]2[NH:32][C:33]3[C:38]([C:39]=2[CH:40]=1)=[CH:37][CH:36]=[CH:35][CH:34]=3.[C:41](#[N:44])[CH:42]=[CH2:43]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOC(C)=O.CCCCCC.O1CCOCC1>[C:41]([CH:42]=[CH:43][C:28]1[CH:29]=[CH:30][C:31]2[NH:32][C:33]3[C:38]([C:39]=2[CH:40]=1)=[CH:37][CH:36]=[CH:35][CH:34]=3)#[N:44]

Participants

9

Reactant 4

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 36780693-iodo-9H-carbazole

Product 1

HCID 57072243HCID 57072243, compoundYield 18.2%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
75 °C

Procedure

To a dioxane solution (10 mL) of triphenylphosphine (139 mg, 0.53 μmol), palladium acetate (40.0 mg, 0.18 μmol) and triethylamine (0.59 μL, 4.23 mmol) were added in this order. The mixture was stirred for 5 minutes at 75° C. A dioxane solution (15 mL) of the compound (1) (1.03 g, 3.52 mmol) and acrylonitrile (0.46 μL, 7.04 mmol) were added thereto, and the reaction solution was heated to reflux for 11.5 hours. Generation of a product was confirmed by TLC (HexH:AcOEt=4:1), and then palladium powder was removed by cotton filtration. The residue was purified by column chromatography (HexH:AcOEt=4:1), and compound (2) (0.14 g, 18%, trans:cis=97:3) was obtained as a white powder. Thus, compound (1) (0.37 g, recovery rate 37%) was recovered as a white powder.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureto reflux for 11.5 hours
  3. custompalladium powder was removed by cotton filtration
  4. customThe residue was purified by column chromatography (HexH:AcOEt=4:1)

Sources & evidence

ORD record
ord-3c4dcfc9206344ec9da3e66f70029c2f
Source dataset
uspto-grants-2013_07
Patent number
US08481714B2

Reaction notes

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