Potassium Carbonate → Methyl 3-(3-pyridinyl)benzoate

HRID 880253

Reaktionsgleichung

Reaktionsgleichung von HRID 880253
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1)=[O:4].Br[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>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].O>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:3]([O:2][CH3:1])=[O:4])[CH:16]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 122863-BromopyridineHCID 312751,4-DioxaneHCID 27347143-(Methoxycarbonyl)benzeneboronic acid

Produkt 1

HCID 4133188Methyl 3-(3-pyridinyl)benzoateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of (3-(methoxycarbonyl)phenyl)boronic acid (600 mg, 3.33 mmol), 3-bromopyridine (479 mg, 3.0 mmol), K2CO3 (1.2 g, 9.0 mmol) and Pd(dppf)Cl2 (50 mg) in a solution of dioxane (10 mL) and H2O (2.5 mL) was stirred at 120° C. for 30 minutes with microwave heating under N2. The catalyst was then filtered and the filtrate concentrated. The residue was then purified by column chromatography to give the desired product and used directly in the next step. (630 mg Yield 90%).

Aufarbeitung

  1. temperaturewith microwave heating under N2
  2. filtrationThe catalyst was then filtered
  3. concentrationthe filtrate concentrated
  4. customThe residue was then purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1847187d0eac452281a98d3d17245484
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993555B2

Verknüpfte Notizen

Wird geladen…