Benzonitrile, 4-[[(4-methylphenyl)sulfonyl]oxy]- → HCID 25221614, compound

HRID 451269Notes

Reaction equation

HRID 451269 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:5][CH:4]=1)#[N:2].[C:20]([C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32]N[CH2:30][CH2:29]2)=[CH:24][CH:23]=1)#[CH:21].[CH3:34]CCCCCC.CCOC(C)=O>>[N:28]1([C:25]2[CH:26]=[CH:27][C:22]([C:20]#[C:21][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)=[CH:23][CH:24]=2)[CH2:33][CH2:32][CH2:34][CH2:30][CH2:29]1

Participants

4

Reactant 3

HCID 11482693Benzonitrile, 4-[[(4-methylphenyl)sulfonyl]oxy]-HCID 20154595HCID 20154595, compoundHCID 21899848Ethylacetate heptane

Product 1

HCID 25221614HCID 25221614, compound

Procedure

This product was prepared from toluene-4-sulfonic acid 4-cyano-phenyl ester and 1-(4-ethynyl-phenyl)-piperazine following the general procedure for the Sonogashira cross-coupling process described above. Chromatography eluent: heptane/EtOAc 9:1; yield (137 mg, 96%); 1H NMR δ (CDCl3): 7.61-7.51 (m, 4H), 7.4 (d, J=8.41 Hz, 2H), 6.85 (d, J=8.42 Hz, 2H), 3.25 (m, 4H), 1.73-153 (m, 6H); LCMS m/z 286.

Workup

  1. customyield (137 mg, 96%)

Sources & evidence

ORD record
ord-438447d1b3284c929fa4519193e0d4a1
Source dataset
uspto-grants-2013_07
Patent number
US08487109B2

Reaction notes

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