Cesium carbonate → 1-[5-Chloro-8-(3-methoxypiperidin-1-yl)quinolin-7-yl]ethanone

HRID 1192615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1192615
FC(F)(F)S(O[C:7]1[C:8]([C:18](=[O:20])[CH3:19])=[CH:9][C:10]([Cl:17])=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2)(=O)=O.[CH3:23][O:24][CH:25]1[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:17][C:10]1[CH:9]=[C:8]([C:18](=[O:20])[CH3:19])[C:7]([N:27]2[CH2:28][CH2:29][CH2:30][CH:25]([O:24][CH3:23])[CH2:26]2)=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[N:15]2

Komponenten

8

Edukt 3

HCID 10796Cesium carbonateHCID 43417443-MethoxypiperidineHCID 58368658HCID 58368658, Verbindung

Produkt 1

HCID 583684851-[5-Chloro-8-(3-methoxypiperidin-1-yl)quinolin-7-yl]ethanoneAusbeute 34,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 634876Binap, (A+-)-KatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A stirred mixture of 7-acetyl-5-chloroquinolin-8-yl trifluoromethanesulfonate (0.12 g, 0.34 mmol, from Example 47, Step 2), 3-methoxypiperidine (0.047 g, 0.41 mmol), palladium acetate (1.5 mg, 0.0068 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (6.3 mg, 0.010 mmol), and cesium carbonate (0.31 g, 0.95 mmol) in tetrahydrofuran (3 mL) was heated at 65° C. overnight. The mixture was cooled, diluted with dichloromethane and filtered. The filtrate was washed with brine, dried over MgSO4 and evaporated under reduced pressure. The residue was purified on silica gel (eluting with 0 to 10% methanol in dichloromethane) to give the desired product (37.3 mg, 34%). LCMS calculated for C17H20ClN2O2 (M+H)+: m/z=319.1; Found: 319.1.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washThe filtrate was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customThe residue was purified on silica gel (eluting with 0 to 10% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-7fd9c1a90b074dc7a3110e778e3669b6
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680108B2

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