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Cesium carbonate → HCID 86690872, Verbindung

HRID 1465570
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1465570
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[N:10]=[C:11]([NH:14][C:15](=[O:22])[C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[S:12][CH:13]=2)=[C:4]([CH3:23])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:31]1[CH:32]=[CH:33][C:34]([N+:37]([O-:39])=[O:38])=[N:35][CH:36]=1>CN(C=O)C>[CH3:8][C:6]1[CH:7]=[C:2]([O:1][C:31]2[CH:36]=[N:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=2)[CH:3]=[C:4]([CH3:23])[C:5]=1[C:9]1[N:10]=[C:11]([NH:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[S:12][CH:13]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 8176205-Bromo-2-nitropyridineHCID 86690827HCID 86690827, Verbindung

Produkt 1

HCID 86690872HCID 86690872, VerbindungAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 5-3 (1.92 g, 5.91 mmol) in DMF (15 mL) was added with cesium carbonate (2.41 g, 7.39 mmol). The reaction mixture was heated at 50° C. for 60 min and added with 5-bromo-2-nitropyridine (24-1, 1.80 g). The reaction mixture was heated at 50° C. for 4.0 h. The solution was quenched with water (40 mL) and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (NH silica gel, hexane/ethyl acetate=3/1-1/3) to give 24 (1.76 g) in 67% yield: 1H NMR (500 MHz, DMSO-d6) δ 8.78 (d, 2 H), 8.42 (d, 1 H), 8.33 (d, 1 H), 7.96 (d, 2 H), 7.63 (m, 1 H), 7.21 (s, 1 H), 7.01 (s, 2 H), 2.08 (s, 6 H), ESI-MS=m/z 447.5 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction mixture was heated at 50° C. for 4.0 h
  2. customThe solution was quenched with water (40 mL)
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by column chromatography (NH silica gel, hexane/ethyl acetate=3/1-1/3)

Quellen und Nachweise

ORD-Eintrag
ord-59f79e2287f24700840204c3be231266
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08999983B2

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