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Cesium carbonate → HCID 58541696, Verbindung

HRID 600257
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 600257
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([CH:15]=2)[CH:13]=[CH:12][S:11]3)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:22]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:27]=CC=C[CH:23]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:27]2[CH:22]=[CH:23][N:14]=[C:10]([S:11][CH3:12])[N:9]=2)[CH:13]=[CH:12][S:11]3)=[CH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 8681986-(4-Fluorophenyl)imidazo[2,1-b][1,3]thiazole

Produkt 1

HCID 58541696HCID 58541696, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysator
HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 6-(4-fluorophenyl)-imidazo[2,1-b]thiazole (J) (6.0 g, 27.6 mmol), 4-iodo-2-thiomethylpyrimidine (10.4 g, 41.3 mmol), cesium carbonate (13.4 g, 41.3 mmol), triphenylphosphine (2.88 g, 11 mmol), and palladium acetate (1.22 g, 5.5 mmol) is added anhydrous dimethylformamide (60 mL). The reaction mixture is sealed and shaken at 80° C. for 12 hours. The reaction was quenched by addition of water (200 mL). The aqueous layer is extracted with ethyl acetate (3×100 mL). The organic phase is washed sequentially with water (100 mL) and a saturated aqueous, sodium chloride solution (100 mL). The organic phase is dried over sodium sulfate, filtered, and the solvent evaporated in vacuo. The crude product is purified by silica gel column chromatography, eluting with a gradient of ethyl acetate/hexane (20-30%). After evaporation of the solvent, 6-(4-fluorophenyl)-5-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[2,1-b]thiazole (K) (Compound CXXXIX, Table 2) is obtained as a white solid (3.5 g, 37%) m.p. 151-152° C.;

Aufarbeitung

  1. customThe reaction mixture is sealed
  2. customThe reaction was quenched by addition of water (200 mL)
  3. extractionThe aqueous layer is extracted with ethyl acetate (3×100 mL)
  4. washThe organic phase is washed sequentially with water (100 mL)
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. customThe crude product is purified by silica gel column chromatography
  9. washeluting with a gradient of ethyl acetate/hexane (20-30%)
  10. customAfter evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-50ce19b79f934a8b8f52a6f55ac7f09f
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07902192B2

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