Allyl chloride → 1-(6-Chloropyridin-3-yl)pent-4-ene-1,2,2-tricarbonitrile

HRID 1795129Notes

Reaction equation

HRID 1795129 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[C:9]([C:12]#[N:13])[C:10]#[N:11])=[CH:4][CH:3]=1.[CH2:14](Cl)[CH:15]=[CH2:16].C[Si]([C:22]#[N:23])(C)C>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O1CCCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([C:22]#[N:23])[C:9]([C:12]#[N:13])([C:10]#[N:11])[CH2:14][CH:15]=[CH2:16])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7850Allyl chlorideHCID 82115Trimethylsilyl cyanideHCID 22185757HCID 22185757, compound

Product 1

HCID 221857521-(6-Chloropyridin-3-yl)pent-4-ene-1,2,2-tricarbonitrileYield 70.9%

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To tetrahydrofuran (13 ml) were added ((6-Chloro-3-pyridyl)methylidene)malononitrile (0.50 g), tris(dibenzylideneacetone)dipalladium chloroform complex (70 mg) and 1,1′-bis(diphenylphosphino)ferrocene (0.15 g) under nitrogen atmosphere, and then allyl chloride (0.41 g) and trimethylsilylcyanide (0.53 g) were added thereto. The solution was stirred at 75° C. for a day. Then the reaction mixture was filtered through silica gel, and concentrated. The residue was subjected to silica gel column chromatography to give 0.48 g of 1-(6-Chloro-3-pyridyl)-1,2,2-tricyano-4-pentene represented by the following formula (hereinafter referred to as the present invention compound (2)).

Workup

  1. filtrationThen the reaction mixture was filtered through silica gel
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-97e505ba97ca43308f83271af7c9fdd4
Source dataset
uspto-grants-2006_04
Patent number
US07026340B2

Reaction notes

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