8-benzyloxy-5-bromo-3-methyl-1H-quinolin-2-one → 8-Benzyloxy-3-methyl-5-vinyl-1H-quinolin-2-one

HRID 244769

Reaktionsgleichung

Reaktionsgleichung von HRID 244769
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](Br)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[C:15]([CH3:20])=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22](C([Sn])=C(CCCC)CCCC)[CH2:23]CC>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:22]=[CH2:23])=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[C:15]([CH3:20])=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 224992118-benzyloxy-5-bromo-3-methyl-1H-quinolin-2-oneHCID 53438229Tri(butyl)vinyltin

Produkt 1

HCID 224991788-Benzyloxy-3-methyl-5-vinyl-1H-quinolin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Palladium tetrakis(triphenylphosphine) (30 mg) is added to a solution of 8-benzyloxy-5-bromo-3-methyl-1H-quinolin-2-one (239 mg) and tributylvinyltin (203 μL) in toluene (7 mL) at room temperature. The reaction mixture is heated for 2 hours at 100° C., cooled to room temperature, evaporated and the product purified by flash column chromatography on silica gel, eluting with 2% ethyl acetate in dichloromethane.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customevaporated
  3. customthe product purified by flash column chromatography on silica gel
  4. washeluting with 2% ethyl acetate in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-90cd000ba6454cce95298836ebc318df
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658673B2

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