Cesium carbonate → 1-(2-fluoroethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 2090418

Reaktionsgleichung

Reaktionsgleichung von HRID 2090418
[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.[F:15][CH2:16][CH2:17]I.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.C(OCC)(=O)C>[F:15][CH2:16][CH2:17][N:12]1[CH:13]=[C:9]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]2)[CH:10]=[N:11]1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 69804Ethane, 1-fluoro-2-iodo-HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Produkt 1

HCID 594022971-(2-fluoroethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.05 g, 0.2 mmol), 1-fluoro-2-iodoethane (0.049 g, 0.28 mmol, SynQuest Labs, Cat. No. 1100-k-18), and cesium carbonate (250 mg, 0.77 mmol) in acetonitrile (1.0 mL) in a sealed reaction vial was heated at 90° C. with stirring overnight. After cooling it was diluted with ethyl acetate. Then the organic solution was washed with water, brine; dried over Na2SO4. After filtration the filtrate was concentrated to yield 19 mg of the product which was directly used in the next step reaction without further purification.

Aufarbeitung

  1. temperatureAfter cooling it
  2. washThen the organic solution was washed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration the filtrate
  5. concentrationwas concentrated

Quellen und Nachweise

ORD-Eintrag
ord-127317c92d264d9c928c81496b27f9c6
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436008B2

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