Toluene → 4-(2-Methoxy-quinolin-5-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1373642Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1373642
C1(C)C=CC=CC=1.Br[C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13]([O:19][CH3:20])=[N:14]2.[C:21]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].CC([O-])(C)C.[Na+]>C(OCC)(=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>[C:24]([O:23][C:21]([N:28]1[CH2:33][CH2:32][N:31]([C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[CH:11]=[CH:12][C:13]([O:19][CH3:20])=[N:14]3)[CH2:30][CH2:29]1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 142209695-Bromo-2-methoxyquinolineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 694222494-(2-Methoxy-quinolin-5-yl)-piperazine-1-carboxylic acid tert-butyl esterAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 27342162-(Dicyclohexylphosphino)biphenylKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A third intermediate compound, 2-Methoxy-5-piperazin-1-yl-quinoline, was produced as follows: To an oven-dried flask, under nitrogen, was added Pd(OAc)2 (0.03 g, 0.13 mmol) and 2-(dicyclohexylphosphino)biphenyl (0.045 g, 0.13 mmol). The flask was evacuated and refilled with nitrogen. The following materials were added in the following order: degassed toluene (10 mL), 5-bromo-2-methoxy-quinoline (0.76 g, 3.23 mmol), 1-Boc-piperazine (0.72 g, 3.87 mmol), and NaOtBu (0.43 g, 4.52 mmol). The mixture was stirred at 80° C. for 1.5 h. After cooling to room temperature, the mixture was diluted with ethyl acetate and filtered through celite. The filtrate was concentrated in vaccuo and purified by chromatography on silica gel (10% EtOAc/Hexane) to give 4-(2-methoxy-quinolin-5-yl)-piperazine-1-carboxylic acid tert-butyl ester as a yellowish solid (0.73 g, 66%). 1H NMR (400 MHz, CDCl3) δ: 8.35 (d, 1H), 7.60 (m, 2H), 7.00 (d, 1H), 6.90 (d, 1H), 4.05 (s, 3H), 3.75 (m, 4H), 3.00 (m, 4H), 1.50 (s, 9H).

Aufarbeitung

  1. customThe flask was evacuated
  2. additionrefilled with nitrogen
  3. additionThe following materials were added in the following order
  4. temperatureAfter cooling to room temperature
  5. filtrationfiltered through celite
  6. concentrationThe filtrate was concentrated in vaccuo
  7. custompurified by chromatography on silica gel (10% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-464fc088001c4c3fb4669856f3448c1f
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07160888B2

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