Cesium carbonate → 2-Chloro-4-((6-nitropyridin-3-yl)oxy)pyridine

HRID 450445

Reaktionsgleichung

Reaktionsgleichung von HRID 450445
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:17][C:18]1[CH:23]=[C:22]([OH:24])[CH:21]=[CH:20][N:19]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:17][C:18]1[CH:23]=[C:22]([O:24][C:2]2[CH:7]=[N:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH:21]=[CH:20][N:19]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 8176205-Bromo-2-nitropyridineHCID 178516507HCID 178516507, Verbindung

Produkt 1

HCID 593227792-Chloro-4-((6-nitropyridin-3-yl)oxy)pyridineAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5-Bromo-2-nitropyridine (1 g, 4.93 mmol) was dissolved in DMF (32 ml) and cooled to 0° C. Cesium carbonate (2.408 g, 7.39 mmol) was added, followed by 2-chloro-4-hydroxypyridine (0.702 g, 5.42 mmol). The mixture was stirred in an 80° C. oil bath for 24 hours. The reaction mixture was then cooled to RT, diluted with ethyl acetate (150 mL), washed with water (2×100 mL) and brine (50 mL), dried (MgSO4), evaporated under reduced pressure and purified via silica gel chromatography (ethyl acetate-hexanes) to yield 2-chloro-4-(6-nitropyridin-3-yloxy)pyridine as a clear oil (0.540 g, 44% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.62 (d, 1H), 8.41 (m, 2H), 8.06 (d, 1H), 7.37 (d, 1H), 7.23 (dd, 1H); MS (ESI) m/z: 252.0 (M+H+).

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled to RT
  2. washwashed with water (2×100 mL) and brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. custompurified via silica gel chromatography (ethyl acetate-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-616f268cd2b846b1a882fad70390c094
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486951B2

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