3-Aminoquinoline → HCID 57808192, Verbindung

HRID 730314

Reaktionsgleichung

Reaktionsgleichung von HRID 730314
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[NH2:18][C:19]1[CH:20]=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOCC.C1(C)C=CC=CC=1>[N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[C:19]([NH:18][C:2]2[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=3)[CH:5]=[CH:4][N:3]=2)[CH:20]=1

Komponenten

8

Edukt 4

HCID 113753-AminoquinolineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 288758632-Chloro-4-(4-trifluoromethylphenyl)pyridine

Produkt 1

HCID 57808192HCID 57808192, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To an oven-dried 50 mL round-bottomed flask were added 2-chloro-4-(4-trifluoromethyl-phenyl)-pyridine (138 mg, 0.54 mmol) and 3-aminoquinoline (Aldrich Chemical Company) (93 mg, 0.64 mmol), followed by anhydrous toluene (45 mL). Nitrogen was bubbled through the above solution via a needle for 1 h. Then palladium acetate (Aldrich Chemical Company) (18 mg, 0.08 mmol) and BINAP (Aldrich Chemical Company) (50 mg, 0.08 mmol) were added to the reaction in one portion, followed by sodium tert-butoxide (Aldrich Chemical Company) (145 mg, 1.5 mmol). The reaction mixture was heated at 90° C. overnight. After cooling to room temperature, the reaction mixture was taken up to ether, and washed with brine. The aqueous layer was extracted with ether (2×) and the combined ether layer was dried over Na2SO4 and concentrated. The residue was purified on a Biotage 40 S column (2.5:1 hexane:EtOAc) to give the title compound as an off-white solid. MS (ESI, pos. ion) m/z: 366 (M+1). Mp: 207.4-207.5° C.

Aufarbeitung

  1. customNitrogen was bubbled through the above solution via a needle for 1 h
  2. temperatureAfter cooling to room temperature
  3. washwashed with brine
  4. extractionThe aqueous layer was extracted with ether (2×)
  5. dry with materialthe combined ether layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified on a Biotage 40 S column (2.5:1 hexane:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-6e358aab378e45fd9115b72342cafc8b
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582657B2

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