Potassium Carbonate → 6-Chloro-4-ethoxy-7-methoxy-2-methyl-3-(4-(4-(trifluoromethoxy)phenoxy)phenyl)quinoline

HRID 1908995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1908995
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([CH3:14])[C:6](I)=[C:5]2[O:16][CH2:17][CH3:18].[F:19][C:20]([F:39])([F:38])[O:21][C:22]1[CH:37]=[CH:36][C:25]([O:26][C:27]2[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=2)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([CH3:14])[C:6]([C:30]1[CH:29]=[CH:28][C:27]([O:26][C:25]3[CH:36]=[CH:37][C:22]([O:21][C:20]([F:19])([F:38])[F:39])=[CH:23][CH:24]=3)=[CH:32][CH:31]=1)=[C:5]2[O:16][CH2:17][CH3:18]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 56776567{4-[4-(Trifluoromethoxy)phenoxy]phenyl}boronic acidHCID 670163176-Chloro-4-ethoxy-3-iodo-7-methoxy-2-methylquinoline

Produkt 1

HCID 670163156-Chloro-4-ethoxy-7-methoxy-2-methyl-3-(4-(4-(trifluoromethoxy)phenoxy)phenyl)quinolineAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of 6-chloro-4-ethoxy-3-iodo-7-methoxy-2-methylquinoline (1.56 g, 4.13 mmol), (4-(4-(trifluoromethoxy)phenoxy)phenyl)boronic acid (1.85 g, 6.20 mmol) and palladium (0) tetrakis triphenylphosphine (239 mg, 0.207 mmol) in degassed dimethylformamide was added 8.25 ml of a 2 N aqueous potassium carbonate solution. The reaction mixture was stirred 18 hours at 85° C., filtered through celite and concentrated in vacuo. The resulting residue was resuspended in dichloromethane and water. The organic layer was extracted with brine, dried over magnesium sulfate and concentrated in vacuo. Purification by silica gel chromatography (0-20% ethyl acetate in dichloromethane) provided 1.18 g 6-chloro-4-ethoxy-7-methoxy-2-methyl-3-(4-(4-(trifluoromethoxy)phenoxy)phenyl)quinoline (57% yield) as a light brown solid. 1H NMR (400 MHz, CDCl3) δ 8.11 (s, 1H), 7.43 (s, 1H), 7.31-7.36 (m, 2H), 7.22-7.26 (m, 2H), 7.07-7.14 (m, 4H), 4.04 (s, 3H), 3.71 (q, J=7.1 Hz, 2H), 2.49 (s, 3H), 1.18 (t, J=7.1 Hz, 3H).

Aufarbeitung

  1. filtrationfiltered through celite and
  2. concentrationconcentrated in vacuo
  3. extractionThe organic layer was extracted with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography (0-20% ethyl acetate in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-90150c1cfc634288b5de637e9e60f0af
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598354B2

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