Reaktion #2354678

ord-e3a05ab4d7f04e5bb3e316ef30e32e23

Reaktionsgleichung

NC(=O)c1cc(-c2ccccc2)cc2c(C3CCNCC3)c[nH]c12
5-phenyl-3-(4-piperidinyl)-1H-indole-7-carboxamide
CCN(CC)CC
triethylamine
CCN(CC)CC
TEA
O=S(=O)(Cl)CCCl
2-chloroethylsulfonyl chloride
C=CS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(-c4ccccc4)cc23)CC1
title compound
Ausbeute 75.0%
C=CS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(-c4ccccc4)cc23)CC1
3-[1-(ethenylsulfonyl)-4-piperidinyl]-5-phenyl-1H-indole-7-carboxamide
Ausbeute 75.0%

Lösungsmittel

Reaktionsbedingungen

Temperatur
0°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe reaction mixture was partitioned between CH2Cl2 (100 mL) and water (50 mL)
  2. 2
    SonstigeThe organic layer was separated
  3. 3
    Extraktionthe aqueous layer was extracted with CH2Cl2 (2×100 mL)
  4. 4
    WaschenThe combined organic phase washed with brine (50 mL)
  5. 5
    Trocknendried over magnesium sulfate
  6. 6
    Filtrationfiltered
  7. 7
    SonstigeThe solvent was removed under reduced pressure
  8. 8
    Filtrationpurified via filtration through an SPE Cartridge (Aminopropyl NH2, 500 mg/6 mL)

Vorschrift

To a solution of 5-phenyl-3-(4-piperidinyl)-1H-indole-7-carboxamide (260 mg, 0.8 mmol) in CH2Cl2 at 0° C., triethylamine (0.44 mL, 3.2 mmol) and 2-chloroethylsulfonyl chloride (0.168 mL, 1.6 mmol) were added. The reaction mixture was stirred at 0° C. for 30 min. The reaction mixture was partitioned between CH2Cl2 (100 mL) and water (50 mL). The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2×100 mL). The combined organic phase washed with brine (50 mL), dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure and purified via filtration through an SPE Cartridge (Aminopropyl NH2, 500 mg/6 mL) to give the title compound (245 mg, 75%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07858796B2uspto-grants-2010_12