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Cesium carbonate → 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]-1lambda6-thietane-1,1-dione

HRID 1051570
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1051570
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:22]1[CH2:25][S:24](=[O:27])(=[O:26])[CH2:23]1>CN(C)C=O>[CH3:1][C:2]1([CH3:14])[C:6]([CH3:7])([CH3:8])[O:5][B:4]([C:9]2[CH:13]=[N:12][N:11]([CH:22]3[CH2:25][S:24](=[O:27])(=[O:26])[CH2:23]3)[CH:10]=2)[O:3]1
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Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 3025393-Bromothietane 1,1-dioxideHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Produkt 1

HCID 1233447443-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]-1lambda6-thietane-1,1-dioneAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A 100-mL round bottomed flask was charged with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.942 g, 4.85 mmol), N,N-dimethylformamide (20 mL) and cesium carbonate (3.16 g, 9.71 mmol). 3-Bromothietane 1,1-dioxide (0.925 g, 5.00 mmol) was added, and the reaction stirred at 60° C. overnight. The reaction mixture was cooled to room temperature and then partitioned between ethyl acetate and water. The aqueous phase was separated and extracted with ethyl acetate. The combined organic phases were washed with water and brine and concentrated to afford an oil. This material was purified via column chromatography on silica gel (eluting with 1:5 ethyl acetate-hexanes) to afford 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)thietane 1,1-dioxide (0.172 g, 12% yield) as a white solid. MS (ESI, pos. ion) m/z 299 [M+H]+.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between ethyl acetate and water
  3. customThe aqueous phase was separated
  4. extractionextracted with ethyl acetate
  5. washThe combined organic phases were washed with water and brine
  6. concentrationconcentrated
  7. customto afford an oil
  8. customThis material was purified via column chromatography on silica gel (eluting with 1:5 ethyl acetate-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-1257f494abb34b9eb122e16073637705
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09388161B2

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