Potassium Hydroxide → 4-(1-cyclopentyl-6-nitro-1H-indol-3-yl)-benzonitrile

HRID 2079898

Reaktionsgleichung

Reaktionsgleichung von HRID 2079898
[OH-].[K+].[N+:3]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=3)=[CH:11][NH:12]2)=[CH:8][CH:7]=1)([O-:5])=[O:4].S(C1C=CC(C)=CC=1)(O[CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)(=O)=O>CS(C)=O>[CH:27]1([N:12]2[C:13]3[C:9](=[CH:8][CH:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:14]=3)[C:10]([C:15]3[CH:16]=[CH:17][C:18]([C:19]#[N:20])=[CH:21][CH:22]=3)=[CH:11]2)[CH2:31][CH2:30][CH2:29][CH2:28]1

Komponenten

5

Edukt 3

HCID 14797Potassium Hydroxide2×HCID 317685Cyclopentyl 4-methylbenzene-1-sulfonate2×HCID 574421974-(6-nitro-1H-indol-3-yl)-benzonitrile

Produkt 1

HCID 574422444-(1-cyclopentyl-6-nitro-1H-indol-3-yl)-benzonitrileAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Versuchsvorschrift

Method M Add KOH pellets (200 mg, 3.42 mmol) to a solution of 4-(6-nitro-1H-indol-3-yl)-benzonitrile, 9, (150 mg, 0.57 mmol) in DMSO (10 mL). After the KOH pellets dissolve, add cyclopenyl tosylate (210 mg, 0.85 mmol) in DMSO (3 mL). Allow the reaction mixture to stir overnight at ambient temperature. Add additional cyclopentyl tosylate (210 mg, 0.85) and allow the reaction mixture to stir for another 6 h. Add still more cyclopentyl tosylate (210 mg, 0.85 mmol) and allow the reaction mixture to stir overnight at ambient temperature. Quench the resulting reaction mixture with 5N HCl/ice. Extract the quenched reaction mixture with EtOAc. Wash the EtOAc extracts with brine. Dry the organic layer over MgSO4, filter, and remove the solvent from the filtrate to provide a solid. Purify by silica gel column chromatography (0-100% EtOAc/hexanes gradient) and collect the fractions and remove the solvent to afford 110 mg (58%) of the title compound. LRMS (API ES+)=332.2 (M+H).

Aufarbeitung

  1. stirringto stir for another 6 h
  2. stirringto stir overnight at ambient temperature
  3. customQuench
  4. customthe resulting reaction mixture with 5N HCl/ice
  5. extractionExtract
  6. customthe quenched reaction mixture with EtOAc
  7. washWash the EtOAc
  8. dry with materialDry the organic layer over MgSO4
  9. filtrationfilter
  10. customremove the solvent from the filtrate
  11. customto provide a solid
  12. customPurify by silica gel column chromatography (0-100% EtOAc/hexanes gradient)
  13. customcollect the fractions
  14. customremove the solvent

Quellen und Nachweise

ORD-Eintrag
ord-59925e9d0a3643939c0cd70ec81fdb67
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932284B2

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