Ethylene glycol diethyl ether → Prinaberel

HRID 491734

Reaktionsgleichung

Reaktionsgleichung von HRID 491734
Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([F:18])[CH:12]=3)=[N:7][C:6]=2[CH:5]=[C:4]([OH:19])[CH:3]=1.[CH2:20](OCCOCC)[CH3:21]>CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[F:18][C:13]1[CH:12]=[C:11]([C:8]2[O:9][C:10]3[C:2]([CH:20]=[CH2:21])=[CH:3][C:4]([OH:19])=[CH:5][C:6]=3[N:7]=2)[CH:16]=[CH:15][C:14]=1[OH:17]

Komponenten

4

Edukt 2

HCID 12375Ethylene glycol diethyl etherHCID 1354573257-Bromo-2-(3-fluoro-4-hydroxyphenyl)benzo[d]oxazol-5-ol

Produkt 1

HCID 656954PrinaberelAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178424406HCID 178424406, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

Dichlorobis(tri-o-tolylphosphine)palladium (II) (0.87 g, 1.1 mmol) was added into a mixture of 7-bromo-2-(3-fluoro-4-hydroxyphenyl)-1,3-benzoxazol-5-ol (7.16 g, 22.1 mmol) tributyl(vinyl)tin (10.5 g, 33.25 mmol) and ethylene glycol diethyl ether (65 mL). The reaction mixture was stirred at 115° C. for 48 h, cooled to room temperature and treated with activated carbon. The mixture was filtered through MgSO4 and concentrated. Purification by flash chromatography, on acidic silica gel (hexanes/EtOAc/CH2Cl2 1/1/1), gave a white solid (4.35 g, 72% yield, m.p. 250-252° C.); MS m/e 272 (M+H)+.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. additiontreated with activated carbon
  3. filtrationThe mixture was filtered through MgSO4
  4. concentrationconcentrated
  5. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b70d09afc80e4106878db31fae9acfba
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531564B2

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