Potassium Carbonate → 6'-bromo-3-[(4-methoxybenzyl)oxy]-4H-1,2'-bipyridin-4-one

HRID 571058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571058
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][O:8][C:9]2[C:14](=[O:15])[CH:13]=[CH:12][NH:11][CH:10]=2)=[CH:5][CH:4]=1.[Br:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21](Br)[N:20]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[Br:18][C:19]1[N:20]=[C:21]([N:11]2[CH:12]=[CH:13][C:14](=[O:15])[C:9]([O:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:17][CH:16]=3)=[CH:10]2)[CH:22]=[CH:23][CH:24]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 122742,6-DibromopyridineHCID 674056953-[(4-Methoxyphenyl)methoxy]-4(1H)-pyridinone

Produkt 1

HCID 866802746'-bromo-3-[(4-methoxybenzyl)oxy]-4H-1,2'-bipyridin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 3-[(4-methoxybenzyl)oxy]pyridin-4(1H)-one (2.31 g, 10 mmol), 2,6-dibromopyridine (4.74 g, 20 mmol), and K2CO3 (3.45 g, 25 mmol) in DMSO was heated at 120° C. overnight. After cooling to rt, the solid was removed by filtration and the DMSO solution was purified by flash chromatography to give 6′-bromo-3-[(4-methoxybenzyl)oxy]-4H-1,2′-bipyridin-4-one. 1H NMR (600 MHz, DMSO): δ 8.42 (dd, J=7.7, 2.4 Hz, 1 H); 8.22 (d, J=2.4 Hz, 1 H); 8.03-7.96 (m, 1 H); 7.96-7.89 (m, 1 H); 7.71 (t, J=7.7 Hz, 1 H); 7.40 (d, J=8.4 Hz, 2 H); 6.96 (d, J=8.4 Hz, 2 H); 6.42 (d, J=7.7 Hz, 1 H); 5.03 (s, 2 H); 3.76 (s, 3 H); 264.1; MS (M+H)+ 387.

Aufarbeitung

  1. temperatureAfter cooling to rt
  2. customthe solid was removed by filtration
  3. customthe DMSO solution was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-36a0d579de1d45d8b3a8e11b67ffe4c4
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09024032B2

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