Acrylonitrile → HCID 59853691, compound

HRID 2374289Notes

Reaction equation

HRID 2374289 reaction equation
I[C:2]1[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][C:3]=1[C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5].[C:28](#[N:31])[CH:29]=[CH2:30].C(N(CC)CC)C>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:28](/[CH:29]=[CH:30]/[C:2]1[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][C:3]=1[C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5])#[N:31]

Participants

6

Reactant 3

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 59853727HCID 59853727, compound

Product 1

HCID 59853691HCID 59853691, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.5 mmol 4-[4-(2-Iodo-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-benzonitrile (Example AG), 6.3 mmol acrylonitrile, 9.0 mmol triethylamine and 0.2 mmol of bis-(triphenylphosphin)-palladium(II)-dichloride in 10 ml dimethylformamide is hold under argon for 2 hours at 80°. The reaction mixture is concentrated. Chromatography (SiO2; cyclohexane/ethyl acetate 9:1) yields the title compound as a slightly yellow solid (105 mg). ). (M+H+: 421.2)

Workup

  1. concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record
ord-63cea6242b494bd6bc79fe25fb5dca6c
Source dataset
uspto-grants-2008_12
Patent number
US07462617B2

Reaction notes

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