Nitrogen → 8-Bromo-2-vinylquinoline

HRID 339668

Reaktionsgleichung

Reaktionsgleichung von HRID 339668
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([Br:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH:13](OB([O-])[O-])=[CH2:14].C(N(CC)CC)C.N#N>C1COCC1.CC(O)C.CCOC(C)=O.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[Br:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([CH:13]=[CH2:14])[CH:11]=[CH:10]2

Komponenten

8

Edukt 4

HCID 947NitrogenHCID 8471TriethylamineHCID 459259512,8-DibromoquinolineHCID 86654342Vinylborate

Produkt 1

HCID 672347808-Bromo-2-vinylquinoline

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 22597222Tetrahydrofuran 2-propanolLösungsmittelHCID 22728543Water ethylacetateLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To 2,8-dibromoquinoline (1.836 g, 6.398 mmol) in THF/IPA (20 mL/10 mL) was added vinylborate (0.9428 g, 7.038 mmol) and triethylamine (0.7769 g, 7.678 mmol). The reaction mixture was purged with N2, and PdCl2(dppf) dichloromethane adduct (0.3685 g, 0.4479 mmol) was added. The reaction was stirred at 55° C. for 12 hours, then cooled to ambient temperature. The reaction mixture was diluted with EtOAc/H2O, and the organic layer was separated and concentrated to provide the crude product.

Aufarbeitung

  1. additionwas added
  2. temperaturecooled to ambient temperature
  3. customthe organic layer was separated
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-038c80a14fc94d0f85367248780f1fd4
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895550B2

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