Reaktion #2354673

ord-ea224ef05d6e49f5a75e75a0684f76a7

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-chloroethanesulfonyl chloride
NC(=O)c1cc(-c2ccccc2)cc2c(C3CCN(S(=O)(=O)CCCl)CC3)c[nH]c12
desired product
Ausbeute 32.0%
NC(=O)c1cc(-c2ccccc2)cc2c(C3CCN(S(=O)(=O)CCCl)CC3)c[nH]c12
3-{1-[(2-chloroethyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide
Ausbeute 32.0%

Lösungsmittel

Reaktionsbedingungen

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

Aufarbeitung

  1. 1
    Sonstigewas partitioned between CH2Cl2 and water
  2. 2
    SonstigeThe organic layer was separated
  3. 3
    Extraktionthe aqueous layer was extracted with CH2Cl2 (2×)
  4. 4
    TrocknenThe combined organic phase was dried over magnesium sulfate
  5. 5
    Sonstigethe solvent removed under reduced pressure
  6. 6
    FiltrationThe resulting residue was purified by 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 (65 mg, 0.2 mmol) in CH2Cl2 (5 mL) at 0° C., triethylamine (0.11 mL, 0.8 mmol) and 2-chloroethanesulfonyl chloride (0.042 mL, 0.4 mmol) were added. After stirring at 0° C. for 30 min. the reaction mixture was partitioned between CH2Cl2 and water. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2×). The combined organic phase was dried over magnesium sulfate and the solvent removed under reduced pressure. The resulting residue was purified by filtration through an SPE Cartridge (Aminopropyl NH2, 500 mg/6 mL) to give the desired product (26 mg, 32%).

Quelle

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