1-Methylpiperazine → 8-(4-Methyl-piperazin-1-yl)-3phenylsulfonylquinoline

HRID 271139

Reaktionsgleichung

Reaktionsgleichung von HRID 271139
I[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])=[CH:7]2.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.CC(C)([O-])C.[Na+]>C1(P[C-]2C=CC=C2)C=CC=CC=1.[C-]1(PC2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][C:8]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:7]3)[CH2:24][CH2:23]1

Komponenten

5

Edukt 3

HCID 531671-MethylpiperazineHCID 114067748-Iodo-3-(phenylsulfonyl)quinolineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 99291628-(4-Methyl-piperazin-1-yl)-3phenylsulfonylquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 133083342Bis(cyclopenta-2,4-dien-1-yl(phenyl)phosphane);iron(2+)Katalysator

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

8-Iodo-3-phenylsulfonyl-quinoline (D6) (190 mg, 0.48 mmol), N-methyl-piperazine (48 mg, 0.48 mmol), sodium tertbutoxide (65 mg, 0.68 mmol), di-palladium tetrakis-(dibenzylidine acetone) [Pd2(dba)3] (88 mg, 0.1 mmol) and 1,1′-diphenylphosphino ferrocene (161 mg, 0.3 mmol) were suspended in degassed dry dioxan (2 ml). The mixture was stirred under argon at 40° C. for 16 hours. The solvent was removed and the residue subjected to flash chromatography on silica gel (eluting with dichloromethane—methanol aq. ammonia) to give the title compound (E1), identical spectroscopically to that prepared by the earlier methods.

Aufarbeitung

  1. customin degassed dry dioxan (2 ml)
  2. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-c336f4147dc6407d896f11bf4a407ad4
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452888B2

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