Pyridine → Ethyl 4,6-dimethyl-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylate

HRID 1662020

Reaktionsgleichung

Reaktionsgleichung von HRID 1662020
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.N1C=CC=CC=1>O1CCOCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4](=[O:9])[C:3]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 66827Phenylboronic AcidHCID 247443Ethyl 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carboxylate

Produkt 1

HCID 13837925Ethyl 4,6-dimethyl-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylateAusbeute 31,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of ethyl 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carboxylate (7.5 g, 0.038 mol), phenylboronic acid (14.1 g, 0.115 mol), cupric acetate (1.38 g, 0.008 mol), pyridine (7.5 mL) in 1,4-dioxane (80 mL) is heated at 80° C. for 96 hours. The solid is filtered off and the filtrate is concentrated. The residue is partitioned with EtOAc (50 mL) and 2N HCl (70 mL), and the precipitate is collected by filtration and washed with EtOAc to give the title product (2.95 g). The EtOAc solution is separated, dried and concentrated. The residue is purified by silica gel column chromatography eluting with PE:acetone (2:1) to give another portion of (0.3 g). (3.25 g, 31.2% yield). MS (m/z): 272.0 (M+H).

Aufarbeitung

  1. filtrationThe solid is filtered off
  2. concentrationthe filtrate is concentrated
  3. customThe residue is partitioned with EtOAc (50 mL) and 2N HCl (70 mL)
  4. filtrationthe precipitate is collected by filtration
  5. washwashed with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-57e49fb0763f41c6a6b13c00bfa96d11
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030302B2

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