Cesium carbonate → 2,7-Dichloro-6-(3,5-dimethoxyphenyl)quinazoline

HRID 56458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 56458
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[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](=[CH:10][C:11]([Cl:12])=[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 593252636-Bromo-2,7-dichloroquinazoline

Produkt 1

HCID 1180361662,7-Dichloro-6-(3,5-dimethoxyphenyl)quinazolineAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 6-bromo-2,7-dichloroquinazoline (3 g, 10.8 mmol), 3,5-dimethoxyphenylboronic acid (2.2 g, 11.9 mmol), cesium carbonate (1.06 g, 32.4 mmol) and Pd(PPh3)2Cl2 (702 mg, 1.08 mmol) in THF (50 mL) and water (10 mL) was degassed with nitrogen three times, and the reaction mixture was stirred at 85° 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:ethyl acetate=10:1˜4:1) to give the title compound (2.0 g, yield: 55%) as a yellowish solid. MS (ES+) requires: 334, 336, C16H12Cl2N2O2, found: 335, 337 [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:ethyl acetate=10:1˜4:1)

Quellen und Nachweise

ORD-Eintrag
ord-b33af2bbe03b45bfb3e6fc220985eba3
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434700B2

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