Cesium carbonate → 2-Chloro-6-(3,5-dimethoxyphenyl)-8-fluoroquinazoline

HRID 56473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 56473
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[N:8]=[C:7]([Cl:13])[N:6]=[CH:5]2.[CH3:14][O:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:13][C:7]1[N:6]=[CH:5][C:4]2[C:9](=[C:10]([F:12])[CH:11]=[C:2]([C:18]3[CH:17]=[C:16]([O:15][CH3:14])[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=3)[CH:3]=2)[N:8]=1

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 4374257(3,5-Dimethoxyphenyl)boronic acidHCID 591992866-Bromo-2-chloro-8-fluoroquinazoline

Produkt 1

HCID 867135972-Chloro-6-(3,5-dimethoxyphenyl)-8-fluoroquinazolineAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 6-bromo-2-chloro-8-fluoroquinazoline (4.0 g, 15.4 mmol), 3,5-dimethoxyphenylboronic acid (4.47 g, 16.9 mmol), cesium carbonate (10.0 g, 30.8 mmol) and Pd(PPh3)2Cl2 (236 mg, 0.77 mmol) in THF (200 mL) and water (10 mL) was degassed with nitrogen three times, and stirred at 80° C. for 3 hours. The reaction mixture was cooled to room temperature and directly concentrated. The residue was purified by silica gel chromatography (petroleum ether:dichloromethane=2:1 to 1:1) to afford the title compound (2.5 g, 51%) as a yellow solid. MS (ES+) C16H12ClFN2O2 requires: 318/320, found: 319/321 [M+H]+.

Aufarbeitung

  1. customwas degassed with nitrogen three times
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationdirectly concentrated
  4. customThe residue was purified by silica gel chromatography (petroleum ether:dichloromethane=2:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-11ee6a2662df4733b3d66f32f632f1c1
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434700B2

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