Reaktion #2354776

ord-f8ba1446a38a44f79f049d9d28597b72

Reaktionsgleichung

O=S(=O)(Cl)c1ccsc1
3-thiophenesulfonyl chloride
NC(=O)c1cc(-c2ccccc2)cc2c(C3CCNCC3)c[nH]c12
5-Phenyl-3-(4-piperidinyl)-1H-indole-7-carboxamide
CCN(C(C)C)C(C)C
diisopropyl ethylamine
→
NC(=O)c1cc(-c2ccccc2)cc2c(C3CCN(S(=O)(=O)c4ccsc4)CC3)c[nH]c12
title compound
Ausbeute 61.0%
NC(=O)c1cc(-c2ccccc2)cc2c(C3CCN(S(=O)(=O)c4ccsc4)CC3)c[nH]c12
5-phenyl-3-[1-(3-thienylsulfonyl)piperidin-4-yl]-1H-indole-7-carboxamide
Ausbeute 61.0%

Edukte

O=S(=O)(Cl)c1ccsc1
3-thiophenesulfonyl chloride
NC(=O)c1cc(-c2ccccc2)cc2c(C3CCNCC3)c[nH]c12
5-Phenyl-3-(4-piperidinyl)-1H-indole-7-carboxamide
CCN(C(C)C)C(C)C
diisopropyl ethylamine

Reagenzien

Keine

Lösungsmittel

ClC(Cl)Cl
CHCl3

Reaktionsbedingungen

Temperatur
-10°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    ExtraktionSolid phase extraction (SPE)
  2. 2
    Waschenan aminopropyl cartridge (500 mg) and elution with CHCl3

Vorschrift

To a solution of 5-Phenyl-3-(4-piperidinyl)-1H-indole-7-carboxamide (31 mg/0.067 mmol) in CHCl3 (1.0 ml) was added diisopropyl ethylamine (3 eq). The mixture was cooled to −10° C. and then added to 3-thiophenesulfonyl chloride. The solution was agitated for 1.5 h. Solid phase extraction (SPE) using an aminopropyl cartridge (500 mg) and elution with CHCl3 followed by ethyl acetate provided the title compound (19 mg 61%). LC/MS: m/z 465 Rt 2.29 min.

Quelle

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