Reaktion #2354672

ord-926cc8cdf5c446aab40b4d21f2d5d256

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=C1c2ccccc2C(=O)N1CCS(=O)(=O)Cl
2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethanesulfonyl chloride
NC(=O)c1cc(-c2ccccc2)cc2c(C3CCN(S(=O)(=O)CCN4C(=O)c5ccccc5C4=O)CC3)c[nH]c12
crude product
Ausbeute 61.0%
NC(=O)c1cc(-c2ccccc2)cc2c(C3CCN(S(=O)(=O)CCN4C(=O)c5ccccc5C4=O)CC3)c[nH]c12
3-(1-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]sulfonyl}-4-piperidinyl)-5-phenyl-1H-indole-7-carboxamide
Ausbeute 61.0%

Lösungsmittel

Reaktionsbedingungen

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

Aufarbeitung

  1. 1
    SonstigeThe reaction mixture was partitioned between CH2Cl2 and water
  2. 2
    SonstigeThe organic layer was separated
  3. 3
    Extraktionthe aqueous layer was extracted with CH2Cl2 (2×)
  4. 4
    WaschenThe combined organic phase washed with brine
  5. 5
    Trocknendried over magnesium sulfate
  6. 6
    Filtrationfiltered
  7. 7
    SonstigeThe solvent was removed under reduced pressure

Vorschrift

To a solution of 5-phenyl-3-(4-piperidinyl)-1H-indole-7-carboxamide (84.8 mg, 0.265 mmol) in CH2Cl2 at 0° C., triethylamine (0.15 mL, 1.06 mmol) and 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethanesulfonyl chloride (87.03 mg, 0.32 mmol) were added. The reaction mixture was stirred 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 washed with brine, dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure to give the crude product (90 mg, 61%).

Quelle

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