4-{3E-[5-(2-Aminophenylethynyl)-2,4-dimethoxyphenyl]acryloyl}benzenesulfonamide → 4-{3E-[5-(1H-indol-2-yl)-2,4-dimethoxyphenyl]acryloyl}benzenesulfonamide

HRID 347358Notes

Reaction equation

HRID 347358 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]#[C:9][C:10]1[C:11]([O:32][CH3:33])=[CH:12][C:13]([O:30][CH3:31])=[C:14](/[CH:16]=[CH:17]/[C:18]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[O:19])[CH:15]=1>C(#N)C.Cl[Pd]Cl>[NH:1]1[C:2]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:8]=[C:9]1[C:10]1[C:11]([O:32][CH3:33])=[CH:12][C:13]([O:30][CH3:31])=[C:14](/[CH:16]=[CH:17]/[C:18]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[O:19])[CH:15]=1

Participants

4

Reactant 1

HCID 694903184-{3E-[5-(2-Aminophenylethynyl)-2,4-dimethoxyphenyl]acryloyl}benzenesulfonamide

Product 1

HCID 210416274-{3E-[5-(1H-indol-2-yl)-2,4-dimethoxyphenyl]acryloyl}benzenesulfonamideYield 83%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

Ex-35E: 4-{3E-[5-(2-Aminophenylethynyl)-2,4-dimethoxyphenyl]acryloyl}benzenesulfonamide (Ex-35D, 0.91 g, 1.97 mmol) was dissolved in acetonitrile (100 ml), heated to reflux, and then PdCl2 (0.035 g, 0.197 mmol) was added. The reaction mixture was kept at reflux for 10 min and cooled to room temperature. Upon cooling, the mixture was filtered to remove any solid material and the filtrate was treated with 3-mercaptopropyl-functionalized silica gel (1.0 g) under stirring for 0.5 h. The mixture was then filtered and concentrated to give crude product, which was recrystallized from EtOAc/hexanes to yield 0.75 g (83%) of 4-{3E-[5-(1H-indol-2-yl)-2,4-dimethoxyphenyl]acryloyl}benzenesulfonamide as a yellow solid, mp 185–187° C. 1H-NMR (DMSO-d6) δ 11.15 (brs, 1H), 8.33(s, 1H), 8.24 (d, J=8 Hz, 2H), 8.07 (d, J=15 Hz, 1H), 7.98 (d, J=8 Hz, 2H), 7.80 (d, J=15 Hz, 1H), 7.41–7.55 (m, 4H), 7.03–7.08 (m, 1H), 6.93–6.99 (m, 2H), 6.83 (s, 1H), 4.04 (s, 3H), 3.99(s, 3H), MS m/z: 463 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperatureat reflux for 10 min
  4. temperatureUpon cooling
  5. filtrationthe mixture was filtered
  6. customto remove any solid material
  7. additionthe filtrate was treated with 3-mercaptopropyl-functionalized silica gel (1.0 g)
  8. filtrationThe mixture was then filtered
  9. concentrationconcentrated
  10. customto give crude product, which
  11. customwas recrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-eaa0c5d080c442b9ae42b8276026bc81
Source dataset
uspto-grants-2007_02
Patent number
US07173129B2

Reaction notes

Loading…