Thiophene-3-boronic acid → Methyl 5-(thiophen-3-yl)nicotinate

HRID 1976594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1976594
[CH3:1][O:2][C:3](=[O:11])[C:4]1(Br)[CH:9]=[CH:8][CH:7]=[N:6][CH2:5]1.[S:12]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13]1>O1CCOCC1>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[C:8]([C:14]2[CH:15]=[CH:16][S:12][CH:13]=2)[CH:7]=[N:6][CH:5]=1

Komponenten

4

Edukt 2

HCID 581760Thiophene-3-boronic acidHCID 23436229HCID 23436229, Verbindung

Produkt 1

HCID 23004855Methyl 5-(thiophen-3-yl)nicotinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Methyl-3-bromo-nicotinate and 3-thiophene boronic acid were dissolved in degassed dioxane (25 mL). To the homogeneous solution was added Pd((Ph3)4P)). The reaction was heated to 90° C. for 18 hours and then cooled to room temperature and concentrated. The residue was taken up into EtOAc and water. The layers were then separated and the organics washed with brine and dried (MgSO4). Flash LC (60% Hexanes/EtOAc) gave the desired product.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. customThe layers were then separated
  4. washthe organics washed with brine
  5. dry with materialdried (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-5f86f036c18f4dd29a7537145d3857c0
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06228871B1

Notizen zur Reaktion

Wird geladen…